New synthetic approach leading to 1- or 1,3-disubstituted 2-thiouracil-5-carboxylates via Dimroth rearrangement of isomeric thiazines

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F15%3A39899682" target="_blank" >RIV/00216275:25310/15:39899682 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.3987/COM-15-13235" target="_blank" >http://dx.doi.org/10.3987/COM-15-13235</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3987/COM-15-13235" target="_blank" >10.3987/COM-15-13235</a>

Result language

angličtina

Original language name

New synthetic approach leading to 1- or 1,3-disubstituted 2-thiouracil-5-carboxylates via Dimroth rearrangement of isomeric thiazines

Original language description

Methyl 1-substituted and 1,3-disubstituted-2-thiouracil-5-carboxylates (3b-d) were prepared using new synthetic approach involving base-catalyzed cyclization of easily available S-[3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl]isothiuronium salts (1a-d) to methyl 2-substituted imino-4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carboxylates (2a-d) and their nucleophile-assisted Dimroth rearrangement to methyl 1-substituted and 1,3-disubstituted-2-thiouracil-5-carboxylates (3b-d). Cyclization step is very sensitive towards the base used - e.g. 1a react with stronger bases or bases in excess to give bis-[3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl] sulfide (4) as the only isolated product.

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

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2015

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

91

Issue of the periodical within the volume

7

Country of publishing house

JP - JAPAN

Number of pages

8

Pages from-to

1377-1384

UT code for WoS article

000358812200002

EID of the result in the Scopus database

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