963-80-4Relevant articles and documents
One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes
Ucar, Sefa,Dastan, Arif
, p. 4013 - 4022 (2020/09/21)
The transition metal-free coupling reactions of unactivated diazanaphthalenes were studied using only lithium tetramethylpiperidine (LiTMP) reagent. Symmetrical and nonsymmetrical bis-diazanaphthalenes were synthesized in moderate to high yield by homo- and cross-coupling of related monomers. In addition, the single-step synthesis of diquinoxalino [2,3-a: 2', 3'c] phenazine and 2,2': 3', 2″ - terquinoxaline using the appropriate equivalent amount of LiTMP was performed. The products were characterized by means of NMR spectroscopy and HRMS spectrometry.
Reactions of the Anion of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile) with Electrophiles
Higashino, Takeo,Kokubo, Hiroyasu,Hayashi, Eisaku
, p. 950 - 961 (2007/10/02)
Reactions of the quinazoline Reissert compound (2) with various electrophiles in the presence of sodium hydride in N,N-dimethylformamide were investigated.The reactions with aldehydes (3) and ketones (12) gave α-aryl (or alkyl)-(7) and α-alkyl-α-aryl (or alkyl)-4-quinazolinylmethyl benzoates (16), respectively.The reaction with ?-deficient heteroaromatics (10a-c) gave 4-heteroarylquinazolines (20a-c).Alkylation (or arylation) with alkyl (or aryl) halides (23a-c) afforded 4-substituted 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitriles (24a-c).The reaction with dimethyl acetylenedicarboxylate proceeded in two ways, giving dimethyl 3-phenylpyrroloquinazoline-1,2-dicarboxylate (27) and dimethyl 3-benzoyl-4-cyano-1,2,3,4-tetrahydro-2,4-ethenoquinazoline-9,10-dicarboxylate (28).The reaction with 2-alkenonitriles (29a,b) resulted in the formation of 2-benzoyl-3-(4-quinanolinyl)alkanonitriles (32a,b).Keywords - rearrangement; substitution; 1,3-dipolar addition; quinazoline Reissert compound anion; α-substituted 4-quinazolinylmethyl benzoate; 4-heteroarylquinazoline; 4-substituted 3,4-dihydro-4-quinazoline carbonitrile; pyrroloquinazoline; 2,4-ethenoquinazoline; 2-benzoyl-3-(4-quinazolinyl)alkanonitrile