1, 3-Diazepinones. 2. The correct structure of squamolone as 1-carbamoyl-2-pyrrolidinone and synthesis of authentic perhydro-1, 3-diazepine-2, 4-dione

VE Marquez, JA Kelley, JS Driscoll

Index: Marquez, Victor E.; Kelley, James A.; Driscoll, John S. Journal of Organic Chemistry, 1980 , vol. 45, # 26 p. 5308 - 5312

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Citation Number: 22

Abstract

The natural product squamolone, previously reported as 4-oxoperhydro-1, 3-diazepin-2-one (l), was found to be instead 1-carbamoyl-2-pyrrolidinone (2). An unequivocal synthesis of the diazepinedione 1 starting from glutaric acid monoarnide (6) produced the desired compound in five steps. Diborane reduction of 1 yielded the known perhydro-l,: l-diazepin-2- 0ne (10, tetramethyleneurea), confirming the seven-membered-ring structure of 1. A ...