The Journal of Organic Chemistry

Secondary. beta.-aminobenzamide and heteroatom directed lithiation in the synthesis of 5, 6-dimethoxyanthranilamides and related compounds

S Bengtsson, T Hoegberg

Index: Bengtsson, Stefan; Hoegberg, Thomas Journal of Organic Chemistry, 1989 , vol. 54, # 19 p. 4549 - 4553

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Citation Number: 23

Abstract

Directed ortho-lithiation strategies have been applied in the synthesis of the dopamine D-2 antagonist (5')-6-amino-5-bromo-2, 3-dimethoxy-N-((1-ethyl-2-pyrrolidiny1) methyl) benzamide (NCQ 318). The secondary 8-amino side chain was found to be a powerful ortho directing group which enabled the direct introduction of the amino group after dilithiation with n-BuLi. Alternatively, 3, 4-dimethoxy-N-(tert-butoxycarbonyl) aniline was ...