The Cyclization of Dinitriles by Anhydrous Halogen Acids. A New Synthesis of Isoquinolines

Francis Johnson; W. A. Nasutavicus

doi:10.1021/jo01058a047

The Cyclization of Dinitriles by Anhydrous Halogen Acids. A New Synthesis of Isoquinolines

Francis Johnson
, W. A. Nasutavicus

Pharmacological Sciences

Stony Brook University

Dow Chemical

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

The action of anhydrous hydrogen chloride, bromide, and iodide, on a number of o-eyanobenzyl cyanides has been examined. While hydrogen chloride effects no cyclization, the other two acids afford 1-halo-3-aminoisoquinolines in excellent yield. Using this method, several polycyclic heterocycles were synthesized. In addition, a number of reactions of 1- bromo-3-aminoisoquinoline itself were studied.

Original language	English
Pages (from-to)	3953-3958
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	27
Issue number	11
DOIs	https://doi.org/10.1021/jo01058a047
State	Published - Nov 1 1962

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title = "The Cyclization of Dinitriles by Anhydrous Halogen Acids. A New Synthesis of Isoquinolines",

abstract = "The action of anhydrous hydrogen chloride, bromide, and iodide, on a number of o-eyanobenzyl cyanides has been examined. While hydrogen chloride effects no cyclization, the other two acids afford 1-halo-3-aminoisoquinolines in excellent yield. Using this method, several polycyclic heterocycles were synthesized. In addition, a number of reactions of 1- bromo-3-aminoisoquinoline itself were studied.",

author = "Francis Johnson and Nasutavicus, \{W. A.\}",

year = "1962",

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Y1 - 1962/11/1

N2 - The action of anhydrous hydrogen chloride, bromide, and iodide, on a number of o-eyanobenzyl cyanides has been examined. While hydrogen chloride effects no cyclization, the other two acids afford 1-halo-3-aminoisoquinolines in excellent yield. Using this method, several polycyclic heterocycles were synthesized. In addition, a number of reactions of 1- bromo-3-aminoisoquinoline itself were studied.

AB - The action of anhydrous hydrogen chloride, bromide, and iodide, on a number of o-eyanobenzyl cyanides has been examined. While hydrogen chloride effects no cyclization, the other two acids afford 1-halo-3-aminoisoquinolines in excellent yield. Using this method, several polycyclic heterocycles were synthesized. In addition, a number of reactions of 1- bromo-3-aminoisoquinoline itself were studied.

UR - https://www.scopus.com/pages/publications/0041904560

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DO - 10.1021/jo01058a047

M3 - Article

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EP - 3958

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -

The Cyclization of Dinitriles by Anhydrous Halogen Acids. A New Synthesis of Isoquinolines

Abstract

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