Syntheses and transformations of azeto[2,1-a]-and -[2,1b]isoquinolines and azeto[1',2': 1,2]pyrido[3,4-b]indoles

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Abstract

The syntheses, transformations and some of the biological features of azeto[2,1-a]and -[2,1-b]isoquinolines and azeto[1',2':1,2]pyrido[3,4- b]indoles are reviewed. Both angularly and linearly fused azetidine derivatives of isoquinolines are known. As concerns the related pyridoindoles, only the angularly fused azeto[1',2':1,2]pyrido[3,4-b]indoles have been prepared and investigated. The most interesting and characteristic transformations of azetoisoquinolines and azeto[1',2':1,2]pyrido[3,4- b]indoles are the ring enlargement reactions; these result, for example, in eight-membered ring derivatives which were difficult to synthesize by earlier methods. Such derivatives are versatile intermediates for the synthesis of biologically important compounds. Some of the azetoisoquinolin-2-ones synthesized and tested to date display weak antibiotic activity. Several other azetoisoquinolines exhibit a wide range of pharmacological activities.

Original languageEnglish
Pages (from-to)1-24
Number of pages24
JournalCurrent Organic Chemistry
Volume3
Issue number1
Publication statusPublished - Jan 1999

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Isoquinolines
Carbolines
Derivatives
Anti-Bacterial Agents

ASJC Scopus subject areas

  • Organic Chemistry

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title = "Syntheses and transformations of azeto[2,1-a]-and -[2,1b]isoquinolines and azeto[1',2': 1,2]pyrido[3,4-b]indoles",
abstract = "The syntheses, transformations and some of the biological features of azeto[2,1-a]and -[2,1-b]isoquinolines and azeto[1',2':1,2]pyrido[3,4- b]indoles are reviewed. Both angularly and linearly fused azetidine derivatives of isoquinolines are known. As concerns the related pyridoindoles, only the angularly fused azeto[1',2':1,2]pyrido[3,4-b]indoles have been prepared and investigated. The most interesting and characteristic transformations of azetoisoquinolines and azeto[1',2':1,2]pyrido[3,4- b]indoles are the ring enlargement reactions; these result, for example, in eight-membered ring derivatives which were difficult to synthesize by earlier methods. Such derivatives are versatile intermediates for the synthesis of biologically important compounds. Some of the azetoisoquinolin-2-ones synthesized and tested to date display weak antibiotic activity. Several other azetoisoquinolines exhibit a wide range of pharmacological activities.",
author = "F. F{\"u}l{\"o}p and G. Bern{\'a}th",
year = "1999",
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T2 - 1,2]pyrido[3,4-b]indoles

AU - Fülöp, F.

AU - Bernáth, G.

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N2 - The syntheses, transformations and some of the biological features of azeto[2,1-a]and -[2,1-b]isoquinolines and azeto[1',2':1,2]pyrido[3,4- b]indoles are reviewed. Both angularly and linearly fused azetidine derivatives of isoquinolines are known. As concerns the related pyridoindoles, only the angularly fused azeto[1',2':1,2]pyrido[3,4-b]indoles have been prepared and investigated. The most interesting and characteristic transformations of azetoisoquinolines and azeto[1',2':1,2]pyrido[3,4- b]indoles are the ring enlargement reactions; these result, for example, in eight-membered ring derivatives which were difficult to synthesize by earlier methods. Such derivatives are versatile intermediates for the synthesis of biologically important compounds. Some of the azetoisoquinolin-2-ones synthesized and tested to date display weak antibiotic activity. Several other azetoisoquinolines exhibit a wide range of pharmacological activities.

AB - The syntheses, transformations and some of the biological features of azeto[2,1-a]and -[2,1-b]isoquinolines and azeto[1',2':1,2]pyrido[3,4- b]indoles are reviewed. Both angularly and linearly fused azetidine derivatives of isoquinolines are known. As concerns the related pyridoindoles, only the angularly fused azeto[1',2':1,2]pyrido[3,4-b]indoles have been prepared and investigated. The most interesting and characteristic transformations of azetoisoquinolines and azeto[1',2':1,2]pyrido[3,4- b]indoles are the ring enlargement reactions; these result, for example, in eight-membered ring derivatives which were difficult to synthesize by earlier methods. Such derivatives are versatile intermediates for the synthesis of biologically important compounds. Some of the azetoisoquinolin-2-ones synthesized and tested to date display weak antibiotic activity. Several other azetoisoquinolines exhibit a wide range of pharmacological activities.

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