Iminoyl chloride

The pyrido[2,l- ][l>2,4]triazines 108 were synthesized from hydrazinopyridine 145 with iminoyl chlorides under mild conditions (Equation 20) <2001JHC205>. 

A further modification of the same process is shown in Equation (14). Using an iminoyl chloride, generated in situ from a nitrile, as the nucleophilic trap leads to the exclusive formation of regioisomer 37. The same regiochemistry was observed in the formation of compound 60 (Equation 15) <2002MOL756>. 

Iminoyl chloride 17 reacted with tetrazoles 18 analogously to afford the 1,2,4-triazoles 19 in excellent yield. The electrocyclizaton of A -imino nitrile imines of the type 20 provided the key step for this general synthesis of 1,2,4-triazoles. Cyanuric chloride, as a triple aromatic imidoyl chloride, was treated with three equivalents of 5-phenyltetrazole to give 21 in 79% yield. ... 

Other related species, such as alkyl chloroformates183, dialkyl carbamyl chlorides1, 77-aryl iminoyl chlorides184 or N-substituted isocyanide dichloride (with alkynyl stannanes only)185 behave in an analogous manner. Acylation of acid chlorides has even proven to be possible with acyltin reagents, or by dimerization of acid chlorides with hexabutylditin and high CO pressure186. 

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