Tetrahedron

N-lithio-N-(2-lithioethyl)-and N-lithio-N-(3-lithiopropyl)-benzamide: direct preparation and synthetic applications of 2-lithioethyl-and 3-lithiopropyl-amine equivalents

J Barluenga, F Foubelo, FJ Fañanás, M Yus

文献索引：Barluenga, Jose; Foubelo, Francisco; Fananas, Francisco J.; Yus, Miguel Tetrahedron, 1989 , vol. 45, # 7 p. 2183 - 2192

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被引用次数: 43

摘要

The successive reaction of 2-chloroethyl and 3-chloropropyl-benzamide with n-butyl-lithium and lithium naphthalenide at temperatures ranging between− 78 and− 50° C leads to N- lithio-N-(2-lithioethyl)-and N-lithio-N-(3-lithio-propyl) benzamide [(8),(9)], which by treatment with different electrophiles (H2O, D2O, Me2S2, CO2, Pr1CHO, PhCHO, Me2CO, Ph2CO, and O2) yields the expected functionalized benzamides [(10),(11)]. The acidic and basic ...