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Heteroannulation through copper catalysis: a novel and highly regio- and stereoselective cyclisation of alkynes leading to (E)-2-(2-arylvinyl)quinazolinones

✍ Scribed by Nitya G Kundu; Gopeswar Chaudhuri

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 86 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00312-4

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✦ Synopsis

2-[N-Alkyl(benzyl)-N-(prop-2%-ynyl)

]aminobenzamides 5 reacted with aryl iodides 2 under palladium-copper catalysis to yield disubstituted alkynes 6-13, which underwent a novel cyclisation in the presence of CuI, K 2 CO 3 , n-Bu 4 NBr in acetonitrile to yield (E)-1-alkyl(benzyl)-3-aryl-2-(2-arylvinyl) quinazolin-4-ones 14-21 in excellent yields instead of the expected benzodiazepinones 22.

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