Quinazolinone Synthesis through Base-Promoted SNAr Reaction of ortho-Fluorobenzamides with Amides Followed by Cyclization

A transition-metal-free synthesis of quinazolin-4-ones by Cs2CO3-promoted SNAr reaction of ortho-fluorobenzamides with amides followed by cyclization in dimethyl sulfoxide has been developed. The present procedure can provide efficient synthetic methods for the formation of both 2-substituted and 2,...

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Published inACS omega Vol. 4; no. 5; pp. 8207 - 8213
Main Authors Iqbal, Muhammad Asif, Lu, Le, Mehmood, Hina, Khan, Dost Muhammad, Hua, Ruimao
Format Journal Article
LanguageEnglish
Published American Chemical Society 31.05.2019
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Summary:A transition-metal-free synthesis of quinazolin-4-ones by Cs2CO3-promoted SNAr reaction of ortho-fluorobenzamides with amides followed by cyclization in dimethyl sulfoxide has been developed. The present procedure can provide efficient synthetic methods for the formation of both 2-substituted and 2,3-disubstituted quinazolin-4-one rings depending on the use of easily available starting materials and an efficient, one-pot protocol for the synthesis of the marketed drug product of methaqualone.
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ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.9b00699