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A Novel Transformation of 3-Alkoxyisoquinolines to 3-Chloroisoquinolines and an Unusual Decyanation of 1,3-Dialkoxy-4-cyano-5,6,7,8-tetrahydroisoquinolines Under Vilsmeier-Haack Conditions

Kasturi, TR and Jois, HRY and Mathew, Lata (1984) A Novel Transformation of 3-Alkoxyisoquinolines to 3-Chloroisoquinolines and an Unusual Decyanation of 1,3-Dialkoxy-4-cyano-5,6,7,8-tetrahydroisoquinolines Under Vilsmeier-Haack Conditions. In: Synthesis, 9 . pp. 743-746.

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Abstract

Isoquinolines I (R=cyano, H; R1=Me, $PhCH_2$) were treated with $POCl_3$ in DMF to yield 3-chloro analogs II, and tetrahydra compounds. III (R and R1 same as above) were prepared in a similar manner. I (R=cyano, R1=Me) was heated with $POCl_3$ in DMF at $80^0$ to give II (R=cyano, R1=Me). Nitrile IV (R2=cyano) with $POCl_3$ in DMF gave IV (R2=CHO), and a bis(1-isoquinolyl)methan derivative.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Georg Thieme Verlag KG Stuttgart New York
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 08 Apr 2008
Last Modified: 27 Aug 2008 13:16
URI: http://eprints.iisc.ernet.in/id/eprint/13414

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