Preparation of 1,2-Dihydroisoquinolines by a Three-Component Reaction under Catalyst-Free Conditions

Kentaro Iso; S. Salprima Yudha; Naoki Asao

doi:10.1055/s-2007-990931

PSP

Preparation of 1,2-Dihydroisoquinolines by a Three-Component Reaction under Catalyst-Free Conditions

Kentaro Iso^a, S. Salprima Yudha^a, Naoki Asao*^a,b
^a Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
^b Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
Fax: +81(22)7953899; e-Mail: asao@mail.tains.tohoku.ac.jp;

Abstract

All articles of this category

Abstract

A variety of 1,2-dihydroisoquinoline derivatives have been efficiently prepared by a three-component reaction using ortho-alkynylbenzaldehydes, primary amines, and pronucleophiles under mild catalyst-free conditions.

Key words

catalyst-free conditions - 1,2-dihydroisoquinoline - direct addition - multicomponent reaction - pronucleophile

Full Text

References

For reviews, see:

1a Chrzanowska M. Rozwadowska MD. Chem. Rev. 2004, 104: 3341

1b Bentley KW. Nat. Prod. Rep. 2004, 21: 395

1c Scott JD. Williams RM. Chem. Rev. 2002, 102: 1669

2 For the solid-supported synthesis of skeletally diverse alkaloid-like compounds, see: Taylor SJ. Taylor AM. Schreiber SL. Angew. Chem. Int. Ed. 2004, 43: 1681

3 Asao N. Yudha SS. Nogami T. Yamamoto Y. Angew. Chem. Int. Ed. 2005, 44: 5526

For other synthetic methods of 1,2-dihydroisoquinolines from o-alkynylarylaldimines, see:

4a Ohtaka M. Nakamura H. Yamamoto Y. Tetrahedron Lett. 2004, 45: 7339

4b Yanada R. Obika S. Kono H. Takemoto Y. Angew. Chem. Int. Ed. 2006, 45: 3822

5 Asao N. Iso K. Yudha SS. Org. Lett. 2006, 8: 4149

6 Addition of CHCl₃ to quaternary protoberberine alkaloids has been reported, see: Marek R. Sečkářová P. Hulová D. Marek J. Dostál J. Sklenář V. J. Nat. Prod. 2003, 66: 481