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Paper | Regular issue | Vol 78, No. 6, 2009, pp.1463-1476
Published online, 17th February, 2009
DOI: 10.3987/COM-08-11627
Synthesis of Indolylindolines Mediated by tert-BuNH2

Oscar R. Suárez-Castillo,* Myriam Meléndez-Rodríguez, Ana L. Morales-García, Indira C. Cano-Escudero, Yaneth M. A. Contreras-Martínez, Martha S. Morales-Ríos, and Pedro Joseph-Nathan

*Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, Hidalgo, 42184, Mexico

Abstract

An improved synthesis of N1-carbomethoxylated indolylindolines 2 from 5-substituted indoles 1, by replacing the previously employed strong acids or toxic metals with t-BuNH2/MeOCOCl in CH2Cl2/H2O, is described. The substituent effect of electron donor or acceptor groups was examined, revealing that electron-deficient indoles are less reactive to dimerization than electron-rich indoles, with 5-cyano and 5-nitroindoles leading to no reaction. A dynamic process caused by the restricted rotation of the N-CO2Me bond of 2 was evidenced by 1H NMR measurements.