TRANSFORMATION OF 1,2-DITHIOLE-3-THIONES INTO 1,6,6alambda4-TRITHIAPENTALENES via REACTION WITH BROMOETHANONES

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F06%3A00015686" target="_blank" >RIV/00216224:14310/06:00015686 - isvavai.cz</a>

Alternative codes found

RIV/68081715:_____/06:00043020

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

TRANSFORMATION OF 1,2-DITHIOLE-3-THIONES INTO 1,6,6alambda4-TRITHIAPENTALENES via REACTION WITH BROMOETHANONES

Original language description

We report the reactions of derivatives of 5-amino-3-thioxo-3H-1,2-dithiole-4-carboxylic acid 1 with bromoethanones and acylation agents. Two different routes were used to obtain the products, 3-(acylmethylidene)-3H-1,2-dithioles 4. These compounds were synthesized by acylation of compounds 1 on the amino group, followed by the reaction with bromoethanones and excess of triethylamine. Another method was based on the inverted order of the mentioned reaction steps and in absence of a base. The treatment of4 with thionyl chloride gave new unsaturated fused lactones 13 whereas thionation led to desired 1,6,6alambda4-trithiapentalenes 5. The structures of products and the reaction mechanisms are discussed.

Czech name

TRANSFORMATION OF 1,2-DITHIOLE-3-THIONES INTO 1,6,6alambda4-TRITHIAPENTALENES via REACTION WITH BROMOETHANONES

Czech description

We report the reactions of derivatives of 5-amino-3-thioxo-3H-1,2-dithiole-4-carboxylic acid 1 with bromoethanones and acylation agents. Two different routes were used to obtain the products, 3-(acylmethylidene)-3H-1,2-dithioles 4. These compounds were synthesized by acylation of compounds 1 on the amino group, followed by the reaction with bromoethanones and excess of triethylamine. Another method was based on the inverted order of the mentioned reaction steps and in absence of a base. The treatment of4 with thionyl chloride gave new unsaturated fused lactones 13 whereas thionation led to desired 1,6,6alambda4-trithiapentalenes 5. The structures of products and the reaction mechanisms are discussed.

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/GA203%2F01%2F1333" target="_blank" >GA203/01/1333: Chalcogen organic compounds - synthesis, transformation and structure elucidation</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2006

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Collection of Czechoslovak Chemical Communications

ISSN

0010-0765

e-ISSN

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Volume of the periodical

71

Issue of the periodical within the volume

5

Country of publishing house

CZ - CZECH REPUBLIC

Number of pages

17

Pages from-to

650-666

UT code for WoS article

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EID of the result in the Scopus database

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