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

摘要

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 electronwithdrawing 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.