Copper-catalysed heteroannulation with alkynes: A general and highly regio- and stereoselective method for the synthesis of (E)-2-(2-arylvinyl) quinazolinones

  • Kundu N
  • Chaudhuri G
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Abstract

A highly regio- and stereoselective procedure for the synthesis of 2-substituted-1,2,3,4-tetrahydroquinazolinones through a two-step procedure, e.g. (i) palladium-copper catalysed C-arylation of terminal alkynes and (ii) copper-catalysed cyclisation of disubstituted alkynes, is described. 2-(N-Alkyl-N-prop-2′-ynyl)amino-N′- p-tolyl benzamides 5a and 5b reacted with aryl iodides 2 in the presence of (Ph3P)2PdCl2(2.5 mol%), CuI (5 mol%), Et3N (5 equiv.) in CH3CN at rt for 16 h to yield the disubstituted alkynes 6-18 which could then be cyclised with CuI (20 mol%), K2CO3(2.5 equiv.), Bu4NBr (1 equiv.) in CH3CN at 80°C for 16-24 h to yield 1-methyl (benzyl)-(E)-2-(2-arylvinyl)-3-p-tolyl-1,2,3,4-tetrahydroquinazolin-4-ones 19-31 in good yields. Only in a few cases, the benzodiazepinones 32-34 could be obtained in poor yield. The synthesis of novel uracil derivatives 35 and 36 is also described. © 2001 Elsevier Science Ltd. All rights reserved.

Author-supplied keywords

  • Copper-catalysed heteroannulation
  • Disubstituted alkynes
  • Palladium-copper catalysis
  • Quinazolinones
  • Terminal alkynes

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Authors

  • Nitya G. Kundu

  • Gopeswar Chaudhuri

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