Synthesis of Polycyclic Tetrahydroisoquinolines and Tetrahydrobenzo[d]azepines from Polymer-Supported Allylglycine

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F22%3A73615674" target="_blank" >RIV/61989592:15310/22:73615674 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.acs.org/doi/pdf/10.1021/acs.joc.2c00039" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acs.joc.2c00039</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.joc.2c00039" target="_blank" >10.1021/acs.joc.2c00039</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of Polycyclic Tetrahydroisoquinolines and Tetrahydrobenzo[d]azepines from Polymer-Supported Allylglycine

Popis výsledku v původním jazyce

Herein, we report a multistep synthesis of polycyclic tetrahydroisoquinolines and tetrahydrobenzo[d]azepines starting from Wang resin-immobilized allylglycine. After sulfonylation with 2/4-nitrobenzenesulfonyl chlorides, Mitsunobu alkylation with various phenylalkynols yielded the corresponding (phenylprop-2-yn-1-yl)-sulfonamides. “Interior” ring-closure enyne metathesis (RCEM) using a Grubbs catalyst 2nd generation (Ru2) yielded functionalized tetrahydroisoquinoline/tetrahydrobenzo[d]azepine intermediates. “East-side” [4+2] cycloaddition with representative dienophiles was followed by the “west-side” construction of different heterocycles using various electrophiles to finally furnish a set of novel molecular frameworks bearing fused [6+6] or [6+7] rings. The developed methodology enables the facile parallel synthesis of novel, pharmacologically promising compounds derived from privileged scaffolds.

Název v anglickém jazyce

Synthesis of Polycyclic Tetrahydroisoquinolines and Tetrahydrobenzo[d]azepines from Polymer-Supported Allylglycine

Popis výsledku anglicky

Herein, we report a multistep synthesis of polycyclic tetrahydroisoquinolines and tetrahydrobenzo[d]azepines starting from Wang resin-immobilized allylglycine. After sulfonylation with 2/4-nitrobenzenesulfonyl chlorides, Mitsunobu alkylation with various phenylalkynols yielded the corresponding (phenylprop-2-yn-1-yl)-sulfonamides. “Interior” ring-closure enyne metathesis (RCEM) using a Grubbs catalyst 2nd generation (Ru2) yielded functionalized tetrahydroisoquinoline/tetrahydrobenzo[d]azepine intermediates. “East-side” [4+2] cycloaddition with representative dienophiles was followed by the “west-side” construction of different heterocycles using various electrophiles to finally furnish a set of novel molecular frameworks bearing fused [6+6] or [6+7] rings. The developed methodology enables the facile parallel synthesis of novel, pharmacologically promising compounds derived from privileged scaffolds.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA21-06553S" target="_blank" >GA21-06553S: Inhibice onkogenních kinas malým molekulami</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2022

Kód důvěrnosti údajů

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

Název periodika

JOURNAL OF ORGANIC CHEMISTRY

ISSN

0022-3263

e-ISSN

1520-6904

Svazek periodika

87

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

15

Strana od-do

"5242–5256"

Kód UT WoS článku

000792258800019

EID výsledku v databázi Scopus

2-s2.0-85127880196