92437-11-1

Upstream product

• 104548-10-9 4-cyano-3-(4-chlorobutyryl)-3,4-dihydroquinazoline 
• 92736-33-9 4-Cyano-4H-quinazoline-3-carboxylic acid ethyl ester 
• 92736-32-8 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile 
• 187336-13-6 1-(4-Chloro-phenyl)-2-phenyl-1-quinazolin-4-yl-ethanol 
• 187336-17-0 1-Furan-2-yl-2-phenyl-1-quinazolin-4-yl-ethanol 
• 95113-40-9 α-phenyl-4-quinazolinylmethyl benzoate 
• 253-82-7 quinazoline 

Relevant academic research and scientific papers

Carbon-carbon bond cleavage of α-hydroxybenzylheteroarenes catalyzed by cyanide ion: Retro-benzoin condensation affords ketones and heteroarenes and benzyl migration affords benzylheteroarenes and arenecarbaldehydes

4-(α-Benzylα-hydroxybenzyl)quinazoline (4a) underwent retro-benzoin condensation catalyzed by cyanide ion to give deoxybenzoin (2a) and quinazoline (5a). Similarly, several nitrogen-containing heteroarenes (4, 9, 12, 16-19) having an α-hydroxybenzyl group at the α-position of the nitrogen underwent retro-benzoin type condensation to afford kelones (2) and heteroarenes (5). However, similar reaction of pyrazolopyrimidines (13, 14, 15) having an α-benzyl-α-hydroxybelzyl group resulted in benzyl migration, giving benzylpyrazolopyrimidines (8) and arenecarbaldehydes (3). Tetrabutylammonium cyanide (11, Bu4NCN) was a more effective cyanide ion donor than KCN (10). The retro-benzoin condensation was applied to the synthesis of 2-substituted quinazolines (38) from 2-chloro-4- aroylquinazolines (34), using the aroyl group as a protecting and electron- withdrawing group.

Preparation and Reactions of Mono-Reissert Compounds and Analogs at the 3,4-Position of Quinazoline

Quinazoline, acid chlorides, and trimethylsilyl cyanide have been converted to mono-Reissert compounds at the 3,4-position of the quinazoline system.Various reactions of these quinazoline Reissert compounds are reported.

Reactions of the Anion of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile) with Electrophiles

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