Formation of Indoles, Dihydroisoquinolines, and Dihydroquinolines by Ruthenium-Catalyzed Heterocyclizations

Alejandro Varela-Fernández; Jesús A. Varela; Carlos Saá

doi:10.1055/s-0032-1316539

Synthesis, Table of Contents

Synthesis 2012; 44(21): 3285-3295
DOI: 10.1055/s-0032-1316539

practical synthetic procedures

Formation of Indoles, Dihydroisoquinolines, and Dihydroquinolines by Ruthenium-Catalyzed Heterocyclizations

Alejandro Varela-Fernández

Departamento de Química Orgánica y Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain, Fax: +34(88)1815704 Email: carlos.saa@usc.es

,

Jesús A. Varela

Departamento de Química Orgánica y Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain, Fax: +34(88)1815704 Email: carlos.saa@usc.es

,

Carlos Saá*

Departamento de Química Orgánica y Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain, Fax: +34(88)1815704 Email: carlos.saa@usc.es

› Author Affiliations

Abstract

All articles of this category

Abstract

Indoles, dihydroisoquinolines, and dihydroquinolines were efficiently prepared by ruthenium-catalyzed heterocyclizations of aromatic homo- and bis-homopropargyl amines/amides in the presence of an amine/ammonium base-acid pair. These regioselective 5-endo and 6-endo cyclizations most probably occur by nucleophilic trapping of key ruthenium-vinylidene intermediates.

Key words

heterocyclizations - indoles - isoquinolines - quinolones - ruthenium - vinylidenes

Full Text

References

References
1 Comprehensive Heterocyclic Chemistry III . Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008

2a Nakamura I, Yamamoto Y. Chem. Rev. 2004; 104: 2127
2b D’Souza DM, Mueller TJ. J. Chem. Soc. Rev. 2007; 36: 1095

For reviews of metal-vinylidenes in catalysis, see:

3a Bruce MI. Chem. Rev. 1991; 91: 197
3b Bruneau C, Dixneuf PH. Acc. Chem. Res. 1999; 32: 311
3c Trost BM. Acc. Chem. Res. 2002; 35: 695
3d Bruneau C, Dixneuf PH. Angew. Chem. Int. Ed. 2006; 45: 2176
3e Trost BM, McClory A. Chem.–Asian J. 2008; 3: 164

4 McDonald FE, Reddy KS, Diaz Y. J. Am. Chem. Soc. 2000; 122: 4304 ; and references cited therein

5a Trost BM, Rhee YH. J. Am. Chem. Soc. 1999; 121: 11680
5b Trost BM, Rhee YH. J. Am. Chem. Soc. 2002; 124: 2528

6 Trost BM, Rhee YH. J. Am. Chem. Soc. 2003; 125: 7482

7a Alcazar E, Pletcher JM, McDonald FE. Org. Lett. 2004; 6: 3877
7b Koo B, McDonald FE. Org. Lett. 2007; 9: 1737

8 Varela-Fernández A, González-Rodríguez C, Varela JA, Castedo L, Saá C. Org. Lett. 2009; 11: 5350
9 Varela-Fernández A, García-Yebra C, Varela JA, Esteruelas MA, Saá C. Angew. Chem. Int. Ed. 2010; 49: 4278
10 McDonald FE, Chatterjee AK. Tetrahedron Lett. 1997; 38: 7687
11 Trost BM, McClory A. Angew. Chem. Int. Ed. 2007; 46: 2074
12 Nair RN, Lee PJ, Rheingold AL, Grotjahn DB. Chem.–Eur. J. 2010; 16: 7992
13 Varela-Fernández A, Varela JA, Saá C. Adv. Synth. Catal. 2011; 353: 1933