Montmorillonite Clay Catalyzed Synthesis of Enantiomerically Pure 1,2,3,4-Tetrahydroquinolines

J. S. Yadav; B. V. S. Reddy; Syeda Meraj; P. Vishnumurthy; K. Narsimulu; A. C. Kunwar

doi:10.1055/s-2006-942528

PAPER

Montmorillonite Clay Catalyzed Synthesis of Enantiomerically Pure 1,2,3,4-Tetrahydroquinolines [1]

J. S. Yadav^a, B. V. S. Reddy*^a, Syeda Meraj^a, P. Vishnumurthy^a, K. Narsimulu^b, A. C. Kunwar^b
^a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
^b Centre for Nuclear Magnetic Resonance, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)7160387; e-Mail: yadavpub@iict.res.in;

Abstract

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Abstract

Arylamines undergo smooth cyclization with 2-deoxy-d-ribose on the surface of montmorillonite KSF clay under mild conditions to afford the corresponding sugar-derived chiral tetrahydroquinolines in high yields with moderate diastereoselectivity. The assignment of the stereochemistry of the product was achieved by various NMR studies.

Key words

2-deoxy sugars - solid acid - arylamines - tetrahydroquinolines

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References

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Molecular mechanics calculations were carried out using Sybyl 6.8 programme on a silicon graphics O₂ workstation.