SYNTHESIS AND REACTIONS OF 1,2,4-TRIAZINE AZIDES WITH TRIPHENYLPHOSPHINE, TRIALKYL PHOSPHITES AND DIALKYL PHOSPHONATES

Abstract

3-Azido-5,6-diphenyl-1,2,4-triazine (1) and 3-azidophenanthro[9,10-e]-1,2,4-triazine (2) are synthesized in high yield (∼75%). 1 and 2 react with triphenylphosphine to afford phosphazenes 5 and 6 with a covalent structure. Reactions of 1 and 2 with trialkylphosphites 3b, c produce phosphazenes 7a, b and 8a, b which have the phosphonium dipolar ion structure, 1 reacts with diethyl phosphonate (4a) to give the phosphoramidate 10a. dissociating to the corresponding amine 11 on reaction with dimethyl phosphonate. Possible reaction mechanisms are proposed for the formation of the new adducts.

Key Words:

• 1,2,4-Triazine azides
• triphenylphosphine
• trialkyl phosphates
• 1,2,4-triazine phosphazenes