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Paper | Regular issue | Vol 63, No. 10, 2004, pp.2287-2307
Published online, 20th August, 2004
DOI: 10.3987/COM-04-10158
New Preparative Route to Hetaryldienes and Azadienes

Ildikó Nagy, György Hajós,* and Zsuzsanna Riedl

*Chemical Research Center, Hungarian Academy of Sciences, H-1525 Budpest, P.O. Box 17, Hungary

Abstract

Tetrazolylacroleins easily available via a four step pathway from 2-aminopyridines proved to be suitable starting compounds for preparation of new tetrazolyldiene systems. Reaction with reagents containing active methylene group gave a series of new dienes, whereas hydroxylamines yielded nitrones. The new dienes underwent cyclizations with electron withdrawn dienophiles to yield tetrazolyl substituted new polycycles, and the nitrones gave fused isoxazolines. The electron demand of the tetrazolyldienes in cycloadditions was interpreted by calculation of frontier orbital energy levels.