Nucleophile-assisted cyclization of β-propargylamino acrylic compounds catalyzed by gold(I): a rapid construction of multisubstituted tetrahydropyridines and their fused derivatives

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00534628" target="_blank" >RIV/61388963:_____/20:00534628 - isvavai.cz</a>

Výsledek na webu

<a href="https://doi.org/10.1039/D0QO00653J" target="_blank" >https://doi.org/10.1039/D0QO00653J</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d0qo00653j" target="_blank" >10.1039/d0qo00653j</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Nucleophile-assisted cyclization of β-propargylamino acrylic compounds catalyzed by gold(I): a rapid construction of multisubstituted tetrahydropyridines and their fused derivatives

Popis výsledku v původním jazyce

Au(I)-catalyzed cyclization of β-propargylamino acrylic derivatives 1, carried out in the presence of methanol, afforded tetrahydropyridines 3 in high isolated yields. An intramolecular version, using substrates with pending OH, NHBoc and 3-MeOC6H4 groups as internal O-, N-, and C-nucleophiles, yielded the ortho-fused cyclic derivatives, namely furo[2,3-b]pyridine derivative 14, pyrrolo[2,3-b]pyridine 18, and an unusual chromeno[3,4-c]pyridine 22 with a new quaternary carbon center. Synthetic utilization of the tetrahydropyridines 3 has been demonstrated by their conversion into substances with privileged pharmacophore scaffold. Thus, four 4-aryl piperidine derivatives 23a,b,f,g were obtained on catalytic hydrogenation of the representative 4-aryl tetrahydropyridines 3a,b,f,g, furthermore, the Diels–Alder cycloaddition of dimethyl acetylene dicarboxylate (DMAD) to dienes 3r–3u, possessing a masked dendralene framework, afforded tetrahydroisoquinolines 25r–25u that can be aromatized to produce polysubstituted isoquinolines, as demonstrated by the conversion of 25r into 27r. These domino transformations thus offer numerous variations of this methodology and reveal its potential for synthetic applications.

Název v anglickém jazyce

Nucleophile-assisted cyclization of β-propargylamino acrylic compounds catalyzed by gold(I): a rapid construction of multisubstituted tetrahydropyridines and their fused derivatives

Popis výsledku anglicky

Au(I)-catalyzed cyclization of β-propargylamino acrylic derivatives 1, carried out in the presence of methanol, afforded tetrahydropyridines 3 in high isolated yields. An intramolecular version, using substrates with pending OH, NHBoc and 3-MeOC6H4 groups as internal O-, N-, and C-nucleophiles, yielded the ortho-fused cyclic derivatives, namely furo[2,3-b]pyridine derivative 14, pyrrolo[2,3-b]pyridine 18, and an unusual chromeno[3,4-c]pyridine 22 with a new quaternary carbon center. Synthetic utilization of the tetrahydropyridines 3 has been demonstrated by their conversion into substances with privileged pharmacophore scaffold. Thus, four 4-aryl piperidine derivatives 23a,b,f,g were obtained on catalytic hydrogenation of the representative 4-aryl tetrahydropyridines 3a,b,f,g, furthermore, the Diels–Alder cycloaddition of dimethyl acetylene dicarboxylate (DMAD) to dienes 3r–3u, possessing a masked dendralene framework, afforded tetrahydroisoquinolines 25r–25u that can be aromatized to produce polysubstituted isoquinolines, as demonstrated by the conversion of 25r into 27r. These domino transformations thus offer numerous variations of this methodology and reveal its potential for synthetic applications.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

Organic Chemistry Frontiers

ISSN

2052-4129

e-ISSN

—

Svazek periodika

7

Číslo periodika v rámci svazku

21

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

12

Strana od-do

3356-3367

Kód UT WoS článku

000582936400027

EID výsledku v databázi Scopus

2-s2.0-85094926961