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Aromatic heteroannulation via ortho lithiation-cyclization of N-acyl-2-bromobenzamides

✍ Scribed by Mukta S. Hendi; Kenneth J. Natalie Jr.; Shivakumar B. Hendi; James A. Campbell; Thomas D. Greenwood; James F. Wolfe

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
281 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

N-acyl-2-bromobenzamides participate in metal-halogen exchange with n-BuLi to form N-acyl-%lithiobenzamides, which undergo cyclization to afford 3alkylidenephthalimidines. The pioneering work of Parhaml first demonstrated that certain ortho-substituted aryllithuim reagents 2 can undergo cyclization to afford products 3 in what may be viewed as an anionic equivalent of the more common Lewis acid-catalyzed protocol for aromatic annulation. Such cyclizations can have a decided advantage over their X @J Ii RLi *

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