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Paper | Regular issue | Vol 92, No. 4, 2016, pp.637-648
Published online, 2nd March, 2016
DOI: 10.3987/COM-15-13353
■ An Efficient Synthesis of 1-(4H-1,2,4-Triazol-3-yl)-Hexahydroquinoline-3-carbonitrile and their Spiro Derivatives from β-Enaminones

S. A. Soliman Ghozlan, Doaa M. Abdelmoniem, Mohamed F. Mady, Amr M. Abdelmoniem, and Ismail A. Abdelhamid*

*Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt

Abstract

A series of N-((1,2,4-triazol-3-yl)-enamine and N-((1,2,3-triazol-4-yl)-enamine were prepared and reacted with α,β-unsaturated nitriles yield novel N-(4H-1,2,4-triazol-3-yl)-hexahydroquinoline-3-carbonitrile and their fused and spiro derivatives. Dimroth type rearrangement of the prepared quinoline derivatives 7a,b and 15a,b was observed in acetic anhydride leading to the formation of substituted pyrimido[4,5-b]quinoline 11a,b, spiro[indoline-3,5'-pyrimido[4,5-b]quinoline] 19 and spiro[indoline-3,5'-[1,3]oxazino[4,5-b]quinoline] 22.