Authors: Chatterjee, Tapasi; Chattopadhyay, Subhagata; Mukhopadhyay, Ranjan; Achari, Basudeb; Chakraborty, Santu; Mukherjee, Alok K.

Source: Journal of Chemical Research, Volume 2005, Number 7, July 2005 , pp. 429-431(3)

Publisher: Science Reviews 2000 Ltd

Abstract:

Attempted hetero Diels-Alder reaction with 2-[(E)-styryl]quinazolin-4(3H)-one (1) and dimethyl acetylenedicarboxylate (2) resulted in unexpected N-3 alkenylation products, 2-[(E)-styryl]-3-[(Z)-1,2-bis(methoxycarbonyl)vinyl]quinazolin-4(3H)-one (4a) and 3-[(E)-1,2-bis(methoxycarbonyl) vinyl] 2-[(E)-styryl]-quinazolin-4(3H)-one (4b) in low yield. Treating 1 and 2-methylquinazolin-4(3H)-one (9) with methyl propiolate (7) also furnished N-3 alkenylation products in low yield. The structure of 4b has been established by X-ray analysis. The molecules of 4b are linked by intermolecular C-H….N hydrogen bonds into centrosymmetric dimers forming R22 (12) rings.

Keywords: N-3 ALKENYLATION, 2-SUBSTITUTED QUINAZOLIN-4(3H)-O

Document Type: Research article

DOI: http://dx.doi.org/10.3184/030823405774309212

Publication date: 2005-07-01

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