Synthesis of Enynoindoles Via Vinyl and Ethynyl Indoles

Leticia  Pérez-Serrano; Luis  Casarrubios; Gema  Domínguez; Patxi  González-Pérez; Javier  Pérez-Castells

doi:10.1055/s-2002-33921

SHORTPAPER

Synthesis of Enynoindoles Via Vinyl and Ethynyl Indoles

Leticia Pérez-Serrano, Luis Casarrubios, Gema Domínguez, Patxi González-Pérez, Javier Pérez-Castells*
Departamento de Química, Facultad de CC, Experimentales y de la Salud, Universidad San Pablo-CEU, Boadilla del Monte 28668-Madrid, Spain
Fax: +34(913)510475; e-Mail: jpercas@ceu.es;

Abstract

All articles of this category

Abstract

A convenient synthesis of indoles bearing allyl, ethynyl, and/or propargyl moieties is described starting from indole or indole-2-carboxylic acid.

Key words

indoles - tandem reactions - enynes - Wittig reactions - alkynes

Full Text

References

1a Molander GA. Schmitt MH. J. Org. Chem. 2000, 65: 3767

1b Beccalli EM. Broggini G. La Rosa C. Passarella D. Pilati T. Terraneo A. Zecchi G. J. Org. Chem. 2000, 65: 8924

1c Ziegler FE. Jeroncic LO. J. Org. Chem. 1991, 56: 3479

1d Jones GB. Moody CJ. Padwa A. Kassir JM. J. Chem. Soc., Perkin Trans. 1 1991, 1721

1e Jones G. B., Moody C. J.; J. Chem. Soc., Perkin Trans. 1; 1989, 2449

2 Pérez-Serrano L. González-Pérez P. Casarrubios L. Domínguez G. Pérez-Castells J. Synlett 2000, 1303

3 Rosillo M. Casarrubios L. Domínguez G. Pérez-Castells J. Tetrahedron Lett. 2001, 42: 7029

4a Dufour B. Motorina I. Fowler FW. Grierson DS. Heterocycles 1994, 37: 1455

4b Eitel M. Pindur U. Heterocycles 1988, 27: 2353

4c Pindur U. Kim M.-H. Tetrahedron Lett. 1988, 29: 3927

4d Pindur U. Heterocycles 1988, 27: 1253

5 For the first synthesis of 2-vinylindole, see: Pindur U. Eitel M. Helv. Chim. Acta 1988, 71: 1060

6 Marco JL. J. Heterocycl. Chem. 1998, 475

7 Bergman J. Venemalm L. J. Org. Chem. 1992, 57: 2495

8 Echavarren AM. J. Org. Chem. 1990, 55: 4255