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

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F20%3A10417729" target="_blank" >RIV/00216208:11160/20:10417729 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11310/20:10417729

Result on the web

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=N3fFpuNwVv" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=N3fFpuNwVv</a>

DOI - Digital Object Identifier

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

Result language

angličtina

Original language name

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

Original language description

Au(I)-catalyzed cyclization of beta-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 orthofused 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.

Czech name

—

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

30104 - Pharmacology and pharmacy

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)

Publication year

2020

Confidentiality

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

Name of the periodical

Organic Chemistry Frontiers

ISSN

2052-4129

e-ISSN

—

Volume of the periodical

7

Issue of the periodical within the volume

21

Country of publishing house

GB - UNITED KINGDOM

Number of pages

12

Pages from-to

3356-3367

UT code for WoS article

000582936400027

EID of the result in the Scopus database

2-s2.0-85094926961