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Paper | Special issue | Vol 82, No. 2, 2010, pp.1251-1266
Published online, 17th August, 2010
DOI: 10.3987/COM-10-S(E)72
A New Synthetic Approach to Some Functionalized Cycl[3.2.2]azine Derivatives

Hideyuki Muranaka, Akikazu Kakehi,* Hiroyuki Suga, and Kennosuke Itoh

*Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan

Abstract

Dehydrogenation of some ethyl 4-oxo-1H-8,8a-dihydro-1,4- thiazino[3,4,5-cd]indolizine-1-carboxylates with 2,3-dichloro-5,6-dicyano-1,4- benzoquinone (DDQ) were examined. No simply dehydrogenated products such as 4-oxo-1H- and 4-oxo-8H-1,4-thiazino[3,4,5-cd]indolizines or their full conjugated enol forms could be obtained, but ethyl cycl[3.2.2]azine-1- carboxylates were directly obtained via the cyclization and the subsequent desulfurization of the 4H-1,4-thiazine ring in the dehydrogenated intermediates.