Solid-phase synthesis of 2,3-dihydrobenzo[f]thiadiazepin-4(5H)-one 1,1-dioxides with three diversity positions

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F16%3A33160845" target="_blank" >RIV/61989592:15110/16:33160845 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15310/16:33160845

Result on the web

<a href="http://pubs.acs.org/doi/ipdf/10.1021/acscombsci.6b00049" target="_blank" >http://pubs.acs.org/doi/ipdf/10.1021/acscombsci.6b00049</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acscombsci.6b00049" target="_blank" >10.1021/acscombsci.6b00049</a>

Result language

angličtina

Original language name

Solid-phase synthesis of 2,3-dihydrobenzo[f]thiadiazepin-4(5H)-one 1,1-dioxides with three diversity positions

Original language description

Synthesis of 2,3-dihydrobenzo[f]thiadiazepin-4(5H)-one 1,1-dioxides from polymer-supported alpha-amino acids is described herein. Different alpha-amino acids immobilized on Wang resin were sulfonylated with various 2-nitrobenzenesulfonyl chlorides. The resulting 2-nitrobenzenesulfonamides were alkylated with alcohols according to the Fukuyama-Mitsunobu procedure. After reduction of the nitro group and cleavage from the polymer support, the final intermediates were reacted with thionyl chloride, and target compounds of good crude purity and acceptable overall yields were obtained. The chiral HPLC studies revealed the partial or full racemization of the amino acid stereocenters. The developed strategy allows for simple production of desired compounds with the application of parallel/combinatorial solid-phase synthesis using commercially available building blocks.

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

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

2016

Confidentiality

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

Name of the periodical

ACS Combinatorial Science

ISSN

2156-8952

e-ISSN

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Volume of the periodical

18

Issue of the periodical within the volume

6

Country of publishing house

US - UNITED STATES

Number of pages

6

Pages from-to

349-354

UT code for WoS article

000377925500012

EID of the result in the Scopus database

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