Mitsunobu C-alkylation of beta-alkoxycarbonyl 2-nitrobenzenesulfones and its use for the rapid synthesis of novel benzothiazine derivatives

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F17%3A73583786" target="_blank" >RIV/61989592:15110/17:73583786 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15310/17:73583786

Result on the web

<a href="http://www.sciencedirect.com/science/article/pii/S0040402017309390" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0040402017309390</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tet.2017.09.017" target="_blank" >10.1016/j.tet.2017.09.017</a>

Result language

angličtina

Original language name

Mitsunobu C-alkylation of beta-alkoxycarbonyl 2-nitrobenzenesulfones and its use for the rapid synthesis of novel benzothiazine derivatives

Original language description

Herein, we report the first examples of the Mitsunobu alkylation of beta-alkoxycarbonyl 2-nitrobenzenesulfones. Wang resin was acylated with alpha-halocarboxylic acids followed by the reaction with 2-nitrothiophenols. After oxidation with m-chloroperbenzoic acid, the immobilized beta-alkoxycarbonyl 2-nitrobenzensulfones were subjected to alkylation with various alcohols. The reaction outcome strongly depended on the selection of the alkylating species. After the reduction of the nitro group, acid-mediated cleavage and subsequent cyclization, the C2-(di)substituted benzothiazin-3(4H)-one 1,1-dioxides were obtained in high crude purities and good overall yields.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Publication year

2017

Confidentiality

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

Name of the periodical

Tetrahedron

ISSN

0040-4020

e-ISSN

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Volume of the periodical

73

Issue of the periodical within the volume

44

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

6296-6306

UT code for WoS article

000413798200007

EID of the result in the Scopus database

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