108-74-7Relevant articles and documents
N-LITHIUM DERIVATIVES OF ALIPHATIC AMINES IN THE SYNTHESIS OF 1-ALKYL-2-PHENYLDIAZENE 2-OXIDES
Shepelev, E. V.,Kostikova, N. N.,Dzhetigenov, B. A.,Kalinin, A. V.
, p. 1291 - 1293 (1991)
Magnesium derivatives of aliphatic amines containing α-hydrogen atoms, in contrast to t-BuNHMgBr, do not form phenylaliphatic diazene oxides upon reaction with nitrobenzene, but rather reduce it to azobenzene and azoxybenzene.Asymmetric diazene oxides are formed when the magnesium derivatives are replaced by lithium derivatives.The reaction of t-BuNHLi with dimethylnitramine gives 1,3,5-trimethyl-1,3,5-triazacyclohexane.
ELECTRONIC STRUCTURES AND THERMOLYSES OF 2-TETRAZENES
Heymanns, Peter,Rademacher, Paul
, p. 2511 - 2518 (1986)
The electronic structures and gas phase termolyses of the cyclic 2-tetrazenes 2 and 3 of open chain 1,1,4,4-tetramethyl-2-tetrazene (1) have been studied by photoelectron spectroscopy.While the six-membered ring compound 2 yields 1-methylmethylenamine (6) and nitrogen as fragments, the seven-membered ring compound 3 is contracted to 1,2-dimethylpyrazolidine (11).The acyclic 2-tetrazene 1 prefers disproportionation to 6 and dimethylamine (7).Based on MNDO calculations the ionization potentials of 1 - 3 were assigned to molecular orbitals.Several conformations of 2 and 3 were calculated.Compound 2 shows a rigid boat conformation with equatorial methyl groups, while 3 can occupy several conformations of similar energies.The different thermal decompositions of 1 - 3 are explained.
Alkylation of 6-mercaptopurine (6-MP) with N-alkyl-N-alkoxycarbonylaminomethyl chlorides: S6-(N-alkyl-N-alkoxycarbonyl)aminomethyl-6-MP prodrug structure effect on the dermal delivery of 6-MP
Siver,Sloan
, p. 66 - 73 (1990)
The S6-(N-alkyl-N-alkoxycarbonyl)aminomethyl-6-MP (6-CARB-6-MP) prodrugs 5-20 were synthesized from the reaction of 6-MP weith N-alkyl-N-alkyoxycarbonylaminomethyl chlorides (4) in dimethyl sulfoxide in overall yields of 5-62%, depending on the N-alkyl and the alkoxy groups involved. The derivatives were fully characterized by spectral and micranalyses. The assignment of the substitution pattern as S6-alkyl was based on comparisons of the UV, 1H NMR and 13C NMR spectra with model compounds. A S6,9-bis-alkyl derivative was obtained from the reaction of 2 equivalents of 4 with 6-MP but the product was unstable and decomposed on standing to a 9-alkyl derivative. The 6-CARB-6-MP prodrugs reverted to 6-MP in water by an S(N)1-type mechanism involving unimolecular charge separation in the transition state of the rate determining step. There was no effect of dermal enzymes on the rate of hydrolysis. The solubilities in isopropyl myristate (IPM) for all of the 6-CARB-6-MP prodrugs were significantly greater than the solubility of 6-MP in IPM but only one prodrug (5) was apparently even as soluble as 6-MP in water. Selected 6-CARB-6-MP prodrugs were examined in diffusion cell experiments. Only the N-methyl-N-methoxycarbonyl derivative 5 gave a steady-state rate of delivery of 6-MP from IPM that was significantly greater than the steady-state rate of delivery of 6-MP from 6-MP in IPM. All the other derivatives gave steady-state rates of delivery of 6-MP from IPM that were either not significantly different, or were significantly lower than the rate obtained from 6-MP in IPM. In all cases, the effect of the 6-CARB-6-MP:IPM suspensions on the permeability of the skin, as determined by the second application flux of theophylline:propylene glycol, was of the same magnitude as the effect of IPM alone.
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Sastry,Curl
, p. 77 (1964)
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Synthesis of N-substituted 1,3,5-triazacyclohexanes catalyzed by starch sulfuric acid
Wu, Hui,Yuan, Rui,Wan, Yu,Yin, Wei,Pang, Li-Ling
experimental part, p. 1097 - 1102 (2012/03/11)
N-substituted 1,3,5-triazacyclohexanes were simply synthesized from the reaction of aromatic or fatty amines and formaldehyde catalyzed by recyclable starch sulfuric acid with good yields at room temperature.
Benzo[b]thiophen-3(2H)-one 1,1-dioxide-a versatile reagent in the synthesis of spiroheterocycles
Cekavicus, Brigita,Vigante, Brigita,Liepinsh, Edvards,Vilskersts, Reinis,Sobolev, Arkadij,Belyakov, Sergey,Plotniece, Aiva,Mekss, Kristaps,Duburs, Gunars
experimental part, p. 9947 - 9952 (2009/04/03)
New applications of benzo[b]thiophen-3(2H)-one 1,1-dioxide have been investigated. The synthesis of a new heterocyclic system 3H,2′H-spiro[benzo[b]thieno[3,2-b]pyridine-3,2′-benzo[b]thiophene] is described and a mechanism for the cyclisation is proposed.
