Browse > Article
http://dx.doi.org/10.5012/bkcs.2002.23.9.1285

A Facile One-Pot Operations of Reduction and Allylation of Nitrobenzaldehydes Mediated by Indium and Their Applications  

Cho, Yong-Seo
Kang, Kyung-Ho
Cha, Joo-Hwan
Choi, Kyung-Il
Pae, Ae-Nim
Koh, Hun-Yeong
Chang, Moon-Ho
Publication Information
Abstract
Various nitrobenzaldehydes were simultaneously allylated and reduced using indium in the presence of HCl in aqueous media to give compounds having both functionality of homoallylic alcohol and aromatic amine. Sequential protection of the amino gro up and oxidation of the anilinyl homoallylic alcohol provided useful precursors of heterocyclic compounds such as dihydroindolones and dihydroquinolones, which could be efficiently synthesized through intramolecular cyclization reaction.
Keywords
Simultaneous reduction-allylation; Indium; Aqueous media;
Citations & Related Records

Times Cited By Web Of Science : 7  (Related Records In Web of Science)
Times Cited By SCOPUS : 9
연도 인용수 순위
1 Lubineau, A.; Auge, J.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998.
2 Moody, C. J.; Pitts, M. P. Synlett 1998, 1028.
3 Chan, T. H.; Isaac, M. B. Pure Appl. Chem. 1996, 68, 919.   DOI   ScienceOn
4 Lee, J. G.; Choi, K. I.; Koh, H. Y.; Kim, Y. S.; Kang, Y. H.; Cho, Y. S. Synthesis 2001, 1, 81.
5 Li, C. J. Chem. Rev. 1993, 93, 2023.   DOI   ScienceOn
6 Cha, J. H.; Pae, A. N.; Choi, K. I.; Cho, Y. S.; Koh, H. Y.; Lee, E. J. Chem. Soc., Perkin Trans 1 2001, 2079.
7 Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937.   DOI   ScienceOn
8 Larock, R. C. Comprehensive Organic Transformatons; VCH: New York, 1989; pp 411-415.
9 Li, C. J.; Chan, T. H. Organic Reaction in Aqueous Media; John Wiley & Sons: New York, 1997.
10 Sauve, G.; Rao, V. S. In Comprehensive Organic Functional Group Transformations; Katrictzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1995; Vol. 2, pp 737-817.
11 Paquette, L. A. In Green Chemistry-Frontier in Benign Chemical Syntheses and Processes; Anastas, P. T., Williamson, T. C., Eds.; Oxford University Press: New York, 1998.
12 Li, C. J. Tetrahedron 1996, 52, 5643.   DOI   ScienceOn
13 Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741.
14 Kabalka, G. W.; Varma, R. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, pp 363-379.
15 Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.   DOI   ScienceOn