[Au]-Catalyzed Cyclization of Propargyl-Tethered Ene-Amides: Substrate-Dependent Access to Tetrasubstituted Pyrroles, Aminophenols, and Dihydropyridines

[Au]-catalyzed and substrate-dependent intramolecular cyclization of sulfonyl ene-amides with a pendant propargyl group afford tetrasubstituted pyrroles, o-aminophenols, or 1,6-dihydropyridine carbaldehydes. While the pyrroles and aminophenols are formed when the propargylic alkyne is terminal, dihy...

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Veröffentlicht in:Journal of organic chemistry Jg. 89; H. 8; S. 5518 - 5535
Hauptverfasser: Suraj, Swamy, K. C. Kumara
Format: Journal Article
Sprache:Englisch
Veröffentlicht: WASHINGTON Amer Chemical Soc 19.04.2024
Schlagworte:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOISOMERIZATION
EPOXY-YNAMIDES
GOLD CATALYSIS
BETA-ENAMINONES
TRANSFORMATIONS
ISSN:0022-3263, 1520-6904
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Zusammenfassung:[Au]-catalyzed and substrate-dependent intramolecular cyclization of sulfonyl ene-amides with a pendant propargyl group afford tetrasubstituted pyrroles, o-aminophenols, or 1,6-dihydropyridine carbaldehydes. While the pyrroles and aminophenols are formed when the propargylic alkyne is terminal, dihydropyridines are formed when internal alkyne is present. Internal alkyne substrates with 2-thienyl and 3-thienyl groups give different types of dihydropyridines. The dihydropyridines so obtained can be readily converted to nicotinaldehydes with concomitant sulfonyl migration upon heating in xylene.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02976