SYNTHESIS OF NOVEL DISPIRO[INDOLINE-3,2'-PYRROLIDINE-3',10''-THIAZOLO[3',2':1,2]PYRIMIDO[5,4-<i>g</i>]INDOLIZINE] DERIVATIVES BY 1,3-DIPOLAR CYCLOADDITION REACTION

Abstract

A number of 7-aryl-5,6-dihydro-7H-thiazolo[3',2':1,2]pyrimido[5,4-g]indolizines were synthesized by the reaction of 4-aryl-3,4,5,6-tetrahydropyrimido[5,4-g]indolizine-2(1H)-thione and dimethyl but-2-ynedioate in good yields. The 1,3-dipolar cycloaddition of azomethine ylide generated in situ from isatin and sarcosine to aryl-5,6-dihydro-7H-thiazolo[3',2':1,2]pyrimido[5,4-g]indolizine afforded novel dispiro[indoline-3,2'-pyrrolidine-3',10''-thiazolo[3',2':1,2]pyrimido[5,4-g]indolizine] in moderate yields. The structures of all the products were characterized thoroughly by NMR, IR, HRMS, together with X-ray crystallographic analysis.