Reactions with Hydrazonoyl Halides 421: Synthesis of Some New 2,3-Dihydro-1,3,4thiadiazoles, 2,3-Dihydro-1,3,4-selenadiazoles and Triazolino[[4], [3]]pyrimidines

Abstract

2,3-Dihydro-1,3,4-thiadiazoles, 2,3-dihydro-1,3,4-selenadiazoles, unsymmetrical azines and triazolino[[4], [3]]pyrimidines were prepared from reaction of (2Z)-3-aza-2-bromo-1-naphto[[1], [2]]furan-2-yl-3-(phenylamino)prop-2-en-1-one (6) with each of potassium thiocyanate, potassium selenocyanate, alkyl carbodithioate, ethyl 6-methyl-2-methylthio-4-substituted 3,4-dihydropyrimidine-5-carboxylate or (ethyl 4-methyl-6-substituted 2-thione-1,3,6-trihydropyrimidine-5-carboxylate). All compounds were elucidated on the basis of elemental analysis, spectral data, and alternative synthesis method whenever possible.