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Regioselective synthesis of N(3)- and O-acylmethyl derivatives of 2-methylthio-4(3H)-quinazolinone

✍ Scribed by Milda M. Burbuliene; Rita Mazeikaite; Povilas Vainilavicius

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
176 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Reaction of 2‐methylthio‐4(3__H__)‐quinazolinone with chloroacetone, ω‐bromoacetophenone or ethyl bromoacetate in different solvents (methanol, acetonitrile, dimethylformamide and toluene) using sodium methoxide or potassium carbonate as a base were studied. Regioselective N~(3)~‐alkylation took place in toluene using potassium carbonate, whereas in dimethylformamide O‐acylmethyl derivatives were obtained. However chloroacetone reacted with 2‐methylthio‐4(3__H__)‐quinazolinone under various conditions to give a mixture of N~(3)~/O‐isomers.

📜 SIMILAR VOLUMES

Convenient synthesis of some 2-substitut
Convenient synthesis of some 2-substituted 4(3H)-quinazolinone derivatives
✍ I. Philipova; G. Dobrikov; K. Krumova; J. Kaneti 📂 Article 📅 2006 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 125 KB

## Abstract magnified image A series of 2‐substituted‐4(3__H__)‐quinazolinones **13‐20** has been synthesized in good yields using the reaction of double lithiated 2‐methylquinazolinone‐4 with a variety of aromatic aldehydes. They have been easily transformed in high yields into the corresponding