Selective Formation of 5- or 6-Membered Rings, 1,3-Thiazolidin-4-one vs. 1,3-Thiazin-4-one, from Acridine Thiosemicarbazides by the Use of Ethyne Acid Esters

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F10%3A00023709" target="_blank" >RIV/60461373:22310/10:00023709 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Selective Formation of 5- or 6-Membered Rings, 1,3-Thiazolidin-4-one vs. 1,3-Thiazin-4-one, from Acridine Thiosemicarbazides by the Use of Ethyne Acid Esters

Original language description

A set of 2-substituted 1-(9,10-dihydroacridin-9-ylidene) thiosemicarbazides 4a-d (H, methyl, ethyl, and n-butyl substituents) were treated with dimethyl acetylenedicarboxylate (DMAD) to yield 5-membered ring 1,3-thiazolidin-4-one products 5a-d. The methyl derivative 4b, upon reaction with methyl propiolate (MP), yielded a 6-membered thiazin-4-one ring product 7b. The structures of the methyl derivative products 5b and 7b were conclusively proven by NMR examinations and compared to X-ray crystallographicanalysis. The ring-chain tautomerism of the thiosemicarbazides, the regio- and stereoselectivity of the reactions, the adopted s-cis conformations of the Z configurations of the products, and the prototropic tautomerism of all the compounds were all substantiated.

Czech name

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Czech description

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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

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2010

Confidentiality

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

Name of the periodical

Heterocycles

ISSN

0385-5414

e-ISSN

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Volume of the periodical

80

Issue of the periodical within the volume

1

Country of publishing house

JP - JAPAN

Number of pages

15

Pages from-to

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UT code for WoS article

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EID of the result in the Scopus database

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