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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/61989592:15310/16:33160845

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

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

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

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

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

ACS Combinatorial Science

ISSN

2156-8952

e-ISSN

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Svazek periodika

18

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

6

Strana od-do

349-354

Kód UT WoS článku

000377925500012

EID výsledku v databázi Scopus

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