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Paper | Regular issue | Vol 36, No. 5, 1993, pp.1027-1038
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6263
Synthesis of N-Alkyl-1,2,4-oxadiazinones as Angiotensin-II (AT1) Receptor Antagonists

Harold N. Weller,* Arthur V. Miller, Kenneth E. J. Dickinson, S. Anders Hedberg, Carol L. Delaney, Randolph P. Serafino, and Suzanne Moreland

*Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 4000, Princeton, NJ 08543-4000, U.S.A.

Abstract

4-Alkyl-1,2,4-oxadiazinones were prepared by regiospecific alkylation of the corresponding 4H-oxadiazinones, which were synthesized by a trimethylaluminum mediated cyclization reaction. Alkylation was regiospecific and generally facile; in one example, however, an unusual fragmentation reaction occurred. A homochiral oxadiazineone was also prepared and alkylated under the described conditions. 4-Biphenylmethyl-1,2,4-oxadiazinones were potent angiotensin-II receptor antagonists.