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Note | Regular issue | Vol 48, No. 2, 1998, pp.303-310
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7996
Synthesis of Novel 3-Aminobenz[c,d]-indol-2(1H)-ones via Tandem Addition-Rearrangement Aryne Pathway

Anlai Wang, Hongming Zhang, and Ed Biehl*

*Department of Chemistry, Southern Methodist University, P.O.Box 750314, Dallas, Texas 75275-0314, U.S.A.

Abstract

The reaction of p-methoxyphenylacetonitrile (3) with 2-bromobenzoic acid (1) and LDA gave 7-amino-6,8-bis-(4’-methoxyphenyl)benz[c,d]indol-2(1H)-one (4) and 2-cyano-3-(4-methoxyphenyl)methyl benzoic acid (5). However, treatment of 3 with 2-bromo-4-methylbenzoic acid (12) and LiTMP yielded 5-phenyl-7-amino-6,8-bis-(4’-methoxyphenyl)benz[c,d]indol-2(1H)-one (13). The structure of 4 was established by single-crystal X-Ray diffractometry.