Intramolecular 1, 3-dipolar cycloaddition of alkyl azide enones and rearrangements of the triazoline intermediates. Formal total synthesis of (.+-.)- …

…, SL Ouyang, DY Hsieh, RC Chang…

Index: Sha, Chin-Kang; Ouyang, Sheng-Lian; Hsieh, Der-Yung; Chang, Ruei-Chih; Chang, Shang-Chia Journal of Organic Chemistry, 1986 , vol. 51, # 9 p. 1490 - 1494

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Citation Number: 50

Abstract

Azido enones 8, 18, 25, 39, and 45, which were prepared by the treatment of the corresponding bromide 7, methanesulfonate 17, chloride 24, bromide 38, and toluenesulfonate 44 with sodium azide, were found to undergo intramolecular 1, 3-dipolar cycloaddition reaction smoothly. Thermolysis of azido enone 8 gave products 15 and 16. Thermolysis of azido enone 18 gave enaminone 22. Thermolysis of azido enone 25 in ...