CAS No.58610-61-0,ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate Suppliers

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2-Pyridinecarboxylicacid, 5-cyano-1,6-dihydro-4-methyl-6-oxo-, ethyl ester

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ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

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2-Pyridinecarboxylicacid, 5-cyano-1,6-dihydro-4-methyl-6-oxo-, ethyl ester

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2-Pyridinecarboxylicacid, 5-cyano-1,6-dihydro-4-methyl-6-oxo-, ethyl ester

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2-Pyridinecarboxylicacid, 5-cyano-1,6-dihydro-4-methyl-6-oxo-, ethyl ester

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1-Butanaminium, N-(4-((4-(butyl(2-sulfoethyl)amino)phenyl)(4-((4-ethoxyphenyl)amino)phenyl)methylene)-2,5-cyclohexadien-1-ylidene)-N-(2-sulfoethyl)-, inner salt, sodium salt (1:1)

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2-Pyridinecarboxylicacid, 5-cyano-1,6-dihydro-4-methyl-6-oxo-, ethyl ester CAS No.58610-61-0

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Hangzhou Fandachem Co.,Ltd

2-Pyridinecarboxylicacid, 5-cyano-1,6-dihydro-4-methyl-6-oxo-, ethyl ester cas 58610-61-0Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by sea, by

2-Pyridinecarboxylicacid, 5-cyano-1,6-dihydro-4-methyl-6-oxo-, ethyl ester cas 58610-61-0

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ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

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ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

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Taizhou volsen chemical Co., Ltd

Cas No.: 58610-61-0 Synonym:2-Pyridinecarboxylicacid, 5-cyano-1,6-dihydro-4-methyl-6-oxo-, ethyl ester;ETHYL 5-CYANO-4-METHYL-6-OXO-1,6-DIHYDROPYRIDINE-2-CARBOXYLATE; Molecular Formula:C10H10N2O3 Molecular Weight: 206.2 Purity: ≥99.% or 95% Packi

ETHYL 5-CYANO-4-METHYL-6-OXO-1,6-DIHYDROPYRIDINE-2-CARBOXYLATE

Cas:58610-61-0

Min.Order:100 Gram

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Synthetic route

: ethyl (3E)-4-ethoxy-2-oxopent-3-enoate

: 107-91-5
cyanoacetic acid amide

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetone Heating;	82%
With potassium carbonate In acetone Reflux;	60%

: ethyl 4-ethoxy-2-oxopent-3-enoate

: 107-91-5
cyanoacetic acid amide

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetone for 10h; Reflux;	65.7%
With potassium carbonate In acetone for 10h; Inert atmosphere; Reflux;	65.7%

: 615-79-2
ethyl 2,4-diketopentanoate

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium chloride / ethanol / 20 °C 2: potassium carbonate / acetone / 10 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: ammonium chloride / ethanol / 20 °C / Inert atmosphere 2: potassium carbonate / acetone / 10 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: ammonium chloride / ethanol / 12 h / 20 °C 2: potassium carbonate / acetone / Reflux View Scheme

: 2969-81-5
4-bromoethylbutanoate

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

A: 154597-41-8
5-Cyano-1-(3-ethoxycarbonyl-propyl)-4-methyl-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester

B: 5-Cyano-6-(3-ethoxycarbonyl-propoxy)-4-methyl-pyridine-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3.5h;	A 20% B 70%

...Expand

: 106-96-7
propargyl bromide

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 181512-47-0
5-Cyano-4-methyl-6-oxo-1-prop-2-ynyl-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	65%

: 420-37-1
trimethoxonium tetrafluoroborate

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: ethyl 5-cyano-6-methoxy-4-methylpyridine-2-carboxylate

Conditions

Conditions	Yield
Stage #1: trimethoxonium tetrafluoroborate; ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate In dichloromethane at 20℃; for 24h; Stage #2: With sodium hydroxide In dichloromethane for 0.166667h;	52.9%

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: ethyl 5-cyano-6-methoxy-4-methylpyridine-2-carboxylate

Conditions

Conditions	Yield
With trimethoxonium tetrafluoroborate In dichloromethane at 20℃; for 24h; Inert atmosphere;	52.9%

: 24424-99-5
di-tert-butyl dicarbonate

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: ethyl 5-((bis(tert-butoxycarbonyl)amino)methyl)-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

Conditions

Conditions	Yield
With hydrogen In methanol at 20℃; for 16h;	33%

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

(MeO)3BF4: (MeO)3BF4

: ethyl 5-cyano-6-methoxy-4-methylpyridine-2-carboxylate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 48h;	32%

: 292638-85-8
acrylic acid methyl ester

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 2-(methoxycarbonyl)-6-cyano-7-methyl-1,5-dioxo-Δ6(8)-tetrahydroindolizine

Conditions

Conditions	Yield
With potassium carbonate 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h; Yield given. Multistep reaction;

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 66917-21-3
7-methyl-9-oxo-9,11-dihydroindolizino[1,2-b]quinoline-8-carbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / NaOH / dimethylformamide; H2O 3: CDI / tetrahydrofuran 4: 75 percent / Ac2O / Heating View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 181512-51-6
5-Cyano-4-methyl-6-oxo-1-prop-2-ynyl-1,6-dihydro-pyridine-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / NaOH / dimethylformamide; H2O View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 2-methoxy-7-methyl-9-oxo-9,11-dihydroindolizino[1,2-b]quinoline-8-carbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / NaOH / dimethylformamide; H2O 3: 83 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (HOBT) / CH2Cl2 4: CH2Cl2 / 20 °C 5: acetonitrile / 6 h / Heating View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 181512-25-4
5-Cyano-4-methyl-6-oxo-1-prop-2-ynyl-1,6-dihydro-pyridine-2-carboxylic acid (4-methoxy-phenyl)-amide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / NaOH / dimethylformamide; H2O 3: 83 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (HOBT) / CH2Cl2 View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 5-Cyano-N-(4-methoxy-phenyl)-4-methyl-6-oxo-1-prop-2-ynyl-1,6-dihydro-pyridine-2-carboximidic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / NaOH / dimethylformamide; H2O 3: 83 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (HOBT) / CH2Cl2 4: CH2Cl2 / 20 °C View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 181512-33-4
2-[(5-Cyano-4-methyl-6-oxo-1-prop-2-ynyl-1,6-dihydro-pyridine-2-carbonyl)-amino]-benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / K2CO3 / dimethylformamide 2: 95 percent / NaOH / dimethylformamide; H2O 3: CDI / tetrahydrofuran View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 58610-65-4
ethyl 2-(6′-cyan-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)acetate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 58610-66-5
6'-cyano-α-ethyl-2',3'-dihydro-5'-oxospiro<1,3-dioxolane-2,1'(5'H)-indolizine>-7'-acetic acid, ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight View Scheme

Yield

Multi-step reaction with 5 steps
1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h
2: 89 percent / conc. HCl / acetic acid / 2 h / Heating
3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating
4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h
5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight
View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 73428-00-9
1,5-dioxo(5'-ethyl-2'H,5'H,6'H-6-oxopyrano)<3',4'-f>-Δ6(8)-tetrahydroindolizine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 8: CCl4 / Heating 9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h
2: 89 percent / conc. HCl / acetic acid / 2 h / Heating
3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating
4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h
5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight
6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr
7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C
8: CCl4 / Heating
9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C
View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 58610-63-2
6-cyano-7-methyl-1,5-dioxo-Δ6(8)-tetrahydroindolizine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 64439-80-1
(+/-)-10-methoxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 8: CCl4 / Heating 9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 10: 2.) p-toluenesulfonic acid / 1.) toluene, reflux, 30 min, 2.) toluene, reflux, 2.5 h 11: 61 percent / oxygen, cupric chloride, dimethylamine / dimethylformamide; H2O / 20 h View Scheme

Yield

Multi-step reaction with 11 steps
1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h
2: 89 percent / conc. HCl / acetic acid / 2 h / Heating
3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating
4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h
5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight
6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr
7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C
8: CCl4 / Heating
9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C
10: 2.) p-toluenesulfonic acid / 1.) toluene, reflux, 30 min, 2.) toluene, reflux, 2.5 h
11: 61 percent / oxygen, cupric chloride, dimethylamine / dimethylformamide; H2O / 20 h
View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 34141-35-0
4-ethyl-1,12-dihydro-14-H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 8: CCl4 / Heating 9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 10: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h View Scheme

Yield

Multi-step reaction with 10 steps
1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h
2: 89 percent / conc. HCl / acetic acid / 2 h / Heating
3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating
4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h
5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight
6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr
7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C
8: CCl4 / Heating
9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C
10: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h
View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: dl-10-hydroxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 8: CCl4 / Heating 9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 10: 2.) p-toluenesulfonic acid / 1.) toluene, reflux, 30 min, 2.) toluene, reflux, 2.5 h 11: 61 percent / oxygen, cupric chloride, dimethylamine / dimethylformamide; H2O / 20 h 12: 48 percent / HBr / 1.5 h / Heating View Scheme

Yield

Multi-step reaction with 12 steps
1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h
2: 89 percent / conc. HCl / acetic acid / 2 h / Heating
3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating
4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h
5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight
6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr
7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C
8: CCl4 / Heating
9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C
10: 2.) p-toluenesulfonic acid / 1.) toluene, reflux, 30 min, 2.) toluene, reflux, 2.5 h
11: 61 percent / oxygen, cupric chloride, dimethylamine / dimethylformamide; H2O / 20 h
12: 48 percent / HBr / 1.5 h / Heating
View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 73427-97-1
6-(acetoxymethyl)-1,1'-(ethylenedioxy)-7-<1'-(ethoxycarbonyl)propyl>-5-oxo-Δ6(8)-tetrahydroindolizine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 8: CCl4 / Heating View Scheme

Yield

Multi-step reaction with 8 steps
1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h
2: 89 percent / conc. HCl / acetic acid / 2 h / Heating
3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating
4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h
5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight
6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr
7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C
8: CCl4 / Heating
View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 31456-25-4
camptothecin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 8: CCl4 / Heating 9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 10: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h 11: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O View Scheme

Yield

Multi-step reaction with 11 steps
1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h
2: 89 percent / conc. HCl / acetic acid / 2 h / Heating
3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating
4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h
5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight
6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr
7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C
8: CCl4 / Heating
9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C
10: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h
11: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O
View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 73427-84-6
4-Hydroxy-4-(2-methoxy-ethyl)-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DMF, 10 min, 2.) DMF, 50 deg C, 24 h 6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 8: CCl4 / Heating 9: 76 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 10: 2.) p-toluenesulfonic acid / 1.) toluene, reflux, 30 min, 2.) toluene, reflux, 3 h 11: 50 percent / oxygen, cupric nitrate trihydrate, dimethylamine / dimethylformamide; H2O / 1 h View Scheme

Yield

Multi-step reaction with 11 steps
1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h
2: 89 percent / conc. HCl / acetic acid / 2 h / Heating
3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating
4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h
5: 1.) potassium tert-butoxide / 1.) DMF, 10 min, 2.) DMF, 50 deg C, 24 h
6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr
7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C
8: CCl4 / Heating
9: 76 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C
10: 2.) p-toluenesulfonic acid / 1.) toluene, reflux, 30 min, 2.) toluene, reflux, 3 h
11: 50 percent / oxygen, cupric nitrate trihydrate, dimethylamine / dimethylformamide; H2O / 1 h
View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 73466-16-7
dl-azacamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 8: CCl4 / Heating 9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 10: 52 percent / 2 h / 100 °C 11: 24 percent / cupric nitrate trihydrate, dimethylamine, oxygen / dimethylformamide; H2O / 1 h View Scheme

Yield

Multi-step reaction with 11 steps
1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h
2: 89 percent / conc. HCl / acetic acid / 2 h / Heating
3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating
4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h
5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight
6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr
7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C
8: CCl4 / Heating
9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C
10: 52 percent / 2 h / 100 °C
11: 24 percent / cupric nitrate trihydrate, dimethylamine, oxygen / dimethylformamide; H2O / 1 h
View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 58610-64-3
7’-methyl-5’-oxo-3’,5’-dihydro-2’H-spiro[[1,3]dioxolane-2,1‘-indolizine]-6’-carbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 73428-01-0
1,5-dioxo<5'-(methoxyethyl)-2'H,5'H,6'H-6-oxopyrano><3',4',-f>-Δ6(8)-tetrahydroindolizine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DMF, 10 min, 2.) DMF, 50 deg C, 24 h 6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 8: CCl4 / Heating 9: 76 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h
2: 89 percent / conc. HCl / acetic acid / 2 h / Heating
3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating
4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h
5: 1.) potassium tert-butoxide / 1.) DMF, 10 min, 2.) DMF, 50 deg C, 24 h
6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr
7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C
8: CCl4 / Heating
9: 76 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C
View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 2-(methoxycarbonyl)-3-<2'-(methoxycarbonyl)ethyl>-6-cyano-7-methyl-1,5-dioxo-Δ6(8)-tetrahydroindolizine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 78 percent / K2CO3 / dimethylformamide / 10 h / Heating View Scheme

: 58610-61-0
ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

: 73427-81-3
dl-12-aza-20-deoxycamptothecin

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 1.) K2CO3 / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h 2: 89 percent / conc. HCl / acetic acid / 2 h / Heating 3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 4: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 5: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 6: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 7: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 8: CCl4 / Heating 9: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 10: 52 percent / 2 h / 100 °C View Scheme

Yield

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