13182-44-0

Upstream product

• 129768-50-9 2-(α-Chlorophenylacetyl)aminobenzamide 
• 1251849-62-3 (S)-(4-oxo-3,4-dihydroquinazolin-2-yl)(phenyl)methyl acetate 
• 13182-47-3 2-Benzoyl-4(3H)-quinazolinone 
• 491-36-1 4-Hydroxyquinazoline 
• 25726-04-9 phenylglyoxylyl chloride 
• 28144-70-9 anthranilic acid amide 
• 129768-52-1 O-Acetyl-(S)-mandelic acid anhydride 
• 129768-51-0 2-(Phenylglyoxylyl)aminobenzamide 
• 438055-43-7 3-tert-butoxycarbonyl-4(3H)-quinazolinone 
• 438055-47-1 (3-tert-butoxycarbonyl-4(3H)-quinazolinon-2-yl)phenylmethanol 

Relevant academic research and scientific papers

Preparation of a useful synthetic precursor, 2-substituted 4(3h)-quinazolinone: Directed lithiation and N3-deprotection of 3-t-butoxycarbonyl-4(3h)-quinazolinone

Directed lithiation of 3-t-butoxycarbonyl-4(3H)-quinazolinone using LDA was accomplished to afford 2-substituted 3-t-butoxycarbonyl-4(3H)-quinazolinones. The t-butoxycarbonyl group of these products was easily deprotected to give key intermediates for the

Synthesis of chrysogine, a metabolite of Penicillium chrysogenum and some related 2-substituted 4-(3H)-quinazolinones

Syntheses of both enantiomers of chrysogine, 2-(α-hydroxyethyl)-4(3H)-quinazolinone, 1 from 2-ammobenzamide are reported. Thus reaction of 2-aminobenzamide and optically active α-acetoxypropionyl chloride gave 9, which upon saponification and cyclization induced by aqueous sodium carbonate at room temperature gave chrysogine. The enantiomeric purity of 1 was determined by NMR. Inversion of (-)-(S)-1, using the Mitsunobo reaction, gave (+)-(R)-1. Reduction of 2-acetyl-4(3H)-qumazolinone 2 with baker's yeast gave the S-enantiomer of 1. The cyclization method used could be extended and a number of 2-(a-hydroxy)alkyl-4-(3H)-quinazolinones are also reported.