Synthesis of 3-deazathiamine

D Hawksley, DA Griffin, FJ Leeper

文献索引：Hawksley, Daniel; Griffin, David A.; Leeper, Finian J. Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 2 p. 144 - 148

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被引用次数: 23

摘要

An efficient ten-step synthesis of deazathiamine is described. The synthesis starts from commercially available α-acetyl-γ-butyrolactone and proceeds via deamination of the key aminothiophene 6. The Gewald synthesis of thiophenes is shown to give a mixture of isomeric products with the unsymmetric ketone used here and so a modified procedure giving a single isomer is developed.

517-23-7

2-乙酰基-γ-丁内酯

~82%

~91%

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[Scheeren, J. W.; Bakker, C. G.; Peperzak, R.; Nivard, R. J. F. Tetrahedron Letters, 1987 , vol. 28, # 16 p. 1821 - 1824]