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

Kód výsledku v 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>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2010

Kód důvěrnosti údajů

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

Název periodika

Heterocycles

ISSN

0385-5414

e-ISSN

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Svazek periodika

80

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

JP - Japonsko

Počet stran výsledku

15

Strana od-do

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Kód UT WoS článku

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EID výsledku v databázi Scopus

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