Synthesis and antifungal properties of dithiocarboxylic acid derivatives. II. Novel preparation of 2-alkylamino-1-cyclopentene-1-dithiocarboxylic acids and some of their derivatives

B. Bordás, P. Sohár, G. Matolcsy, P. Berencsi

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Abstract

2-Methylamino-1-cyclopentene-1-dithiocarboxylic acid (II) can be obtained in low yield from cyclopentanone with carbon disulfide and methylamine; no other 2-alkylamino analogs can be synthesized. The amino group of 2-amino-1-cyclopentene-1-dithiocarboxylic acid (I) and that of its methyl ester (VII) can be substituted by the alkylamino group by an amine exchange reaction, yielding the corresponding 2-alkylamino-1-cyclopentene-1-dithiocarboxylic acid (II) or its methyl ester (III-V, VIII-XII), respectively. The structures, including tautomeric forms of the synthesized compounds, were proved by ir and nmr spectroscopy.

Original languageEnglish
Pages (from-to)1727-1730
Number of pages4
JournalJournal of Organic Chemistry
Volume37
Issue number11
Publication statusPublished - 1972

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Cyclopentanes
Derivatives
Acids
Esters
Carbon Disulfide
Amines
Spectroscopy

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Synthesis and antifungal properties of dithiocarboxylic acid derivatives. II. Novel preparation of 2-alkylamino-1-cyclopentene-1-dithiocarboxylic acids and some of their derivatives",
abstract = "2-Methylamino-1-cyclopentene-1-dithiocarboxylic acid (II) can be obtained in low yield from cyclopentanone with carbon disulfide and methylamine; no other 2-alkylamino analogs can be synthesized. The amino group of 2-amino-1-cyclopentene-1-dithiocarboxylic acid (I) and that of its methyl ester (VII) can be substituted by the alkylamino group by an amine exchange reaction, yielding the corresponding 2-alkylamino-1-cyclopentene-1-dithiocarboxylic acid (II) or its methyl ester (III-V, VIII-XII), respectively. The structures, including tautomeric forms of the synthesized compounds, were proved by ir and nmr spectroscopy.",
author = "B. Bord{\'a}s and P. Soh{\'a}r and G. Matolcsy and P. Berencsi",
year = "1972",
language = "English",
volume = "37",
pages = "1727--1730",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
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TY - JOUR

T1 - Synthesis and antifungal properties of dithiocarboxylic acid derivatives. II. Novel preparation of 2-alkylamino-1-cyclopentene-1-dithiocarboxylic acids and some of their derivatives

AU - Bordás, B.

AU - Sohár, P.

AU - Matolcsy, G.

AU - Berencsi, P.

PY - 1972

Y1 - 1972

N2 - 2-Methylamino-1-cyclopentene-1-dithiocarboxylic acid (II) can be obtained in low yield from cyclopentanone with carbon disulfide and methylamine; no other 2-alkylamino analogs can be synthesized. The amino group of 2-amino-1-cyclopentene-1-dithiocarboxylic acid (I) and that of its methyl ester (VII) can be substituted by the alkylamino group by an amine exchange reaction, yielding the corresponding 2-alkylamino-1-cyclopentene-1-dithiocarboxylic acid (II) or its methyl ester (III-V, VIII-XII), respectively. The structures, including tautomeric forms of the synthesized compounds, were proved by ir and nmr spectroscopy.

AB - 2-Methylamino-1-cyclopentene-1-dithiocarboxylic acid (II) can be obtained in low yield from cyclopentanone with carbon disulfide and methylamine; no other 2-alkylamino analogs can be synthesized. The amino group of 2-amino-1-cyclopentene-1-dithiocarboxylic acid (I) and that of its methyl ester (VII) can be substituted by the alkylamino group by an amine exchange reaction, yielding the corresponding 2-alkylamino-1-cyclopentene-1-dithiocarboxylic acid (II) or its methyl ester (III-V, VIII-XII), respectively. The structures, including tautomeric forms of the synthesized compounds, were proved by ir and nmr spectroscopy.

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