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One‐Pot Synthesis of 3‐Acetyl‐2‐aryl‐3,4‐dihydroquinazolines from N ‐[2‐(Azidomethyl)phenyl]benzamides Utilizing Intramolecular Aza‐ Wittig Reaction
Author(s) -
Kobayashi Kazuhiro,
Matsumoto Naoki,
Nagashima Mika,
Inouchi Hiroki
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400316
Subject(s) - chemistry , intramolecular force , wittig reaction , phosphorane , aryl , acetylation , medicinal chemistry , sequence (biology) , stereochemistry , organic chemistry , alkyl , biochemistry , gene
A new and convenient method for the preparation of 3,4‐dihydroquinazolines 5 with aryl and Ac groups at C(2) and N(3), respectively, has been developed. The key sequence is the formation of aza‐phosphorane intermediates by the reaction of N ‐[2‐(azidomethyl)phenyl]benzamides 1 with Ph 3 P, followed by intramolecular aza‐ Wittig reaction and 3‐acetylation, which can be conducted in one‐pot.