An Efficient General Synthesis of Novel Functionalized Tetrahydroisoquinoline Derived Enamines via Polarized Ketene N,S-Acetals

Okram Barun; Pramod Kumar Mohanta; H. Ila; H. Junjappa

doi:10.1055/s-2000-6612

Synlett 2000; 2000(5): 0653-0657
DOI: 10.1055/s-2000-6612

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An Efficient General Synthesis of Novel Functionalized Tetrahydroisoquinoline Derived Enamines via Polarized Ketene N,S-Acetals

Okram Barun^* , Pramod Kumar Mohanta, H. Ila, H. Junjappa

^*Department of Chemistry, Indian Institute of Technology, Kanpur-208016, India; Fax 91-0512-597436, 91-0512-590260; E-mail: hila@iitk.ac.in

Abstract

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An efficient general method for the synthesis of novel functionalized heterocyclic enaminones/esters/nitriles derived from tetrahydroisoquinoline has been developed by HgCl₂ (or POCl₃) induced cyclocondensation of newly prepared polarized ketene N,S-acetals from 3,4-dimethoxyphenylethylamine and polarized ketene dithioacetals.

1-(substituted-methylene)-1,2,3,4-tetrahydroisoquinolines - polarized ketene N,S-acetals - polarized ketene dithioacetals - heterocyclic enaminones - heterocyclic enaminonitrile

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