Reaction of 3-(substituted phenyl)-6-methyl-1,6-dihydro-1,2,4,5-tetrazine with aryl isocyanates,chloroformates and acyl chlorides

Abstract

23 1,6-Dihydro-1,2,4,5-tetrazine derivatives 2a-n, 3a-f, 4a-c have been synthesised by reaction of 3-(substituted phenyl)-6-methyl-1,6-dihydro-1,2,4,5-tetrazines (1a-c) with aryl isocyanates chloroformates and acyl chlorides, respectively. The yields were in the range 42-97%. It was found that a base promotes the reactions, and electron-withdrawing substituents in the benzene ring at C3 were beneficial to the yield. On substitution of the N(1) atom the conformation of the products at C(6) was inverted.