Nucleophile-assisted cyclization of beta-propargylamino acrylic compounds catalyzed by gold(I): a rapid construction of multisubstituted tetrahydropyridines and their fused derivatives
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F20%3A39916638" target="_blank" >RIV/00216275:25310/20:39916638 - isvavai.cz</a>
Result on the web
<a href="https://pubs.rsc.org/en/content/articlelanding/2020/qo/d0qo00653j/unauth#!divAbstract" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2020/qo/d0qo00653j/unauth#!divAbstract</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d0qo00653j" target="_blank" >10.1039/d0qo00653j</a>
Alternative languages
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
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic Chemistry Frontiers
ISSN
2052-4110
e-ISSN
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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