[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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| Published in: | Journal of organic chemistry Vol. 89; no. 8; pp. 5518 - 5535 |
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19.04.2024
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| ISSN: | 0022-3263, 1520-6904 |
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| Abstract | [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. |
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| AbstractList | [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. [Au]-catalyzed and substrate-dependent intramolecular cyclization of sulfonyl ene-amides with a pendant propargyl group afford tetrasubstituted pyrroles, -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. |
| Author | Swamy, K. C. Kumara Suraj |
| Author_xml | – sequence: 1 surname: Suraj fullname: Suraj – sequence: 2 givenname: K. C. Kumara orcidid: 0000-0002-7617-706X surname: Swamy fullname: Swamy, K. C. Kumara email: kckssc@uohyd.ac.in organization: Univ Hyderabad, Sch Chem, Hyderabad 500 046, Telangana, India |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38598775$$D View this record in MEDLINE/PubMed |
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| Snippet | [Au]-catalyzed and substrate-dependent intramolecular cyclization of sulfonyl ene-amides with a pendant propargyl group afford tetrasubstituted pyrroles,... |
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| StartPage | 5518 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | [Au]-Catalyzed Cyclization of Propargyl-Tethered Ene-Amides: Substrate-Dependent Access to Tetrasubstituted Pyrroles, Aminophenols, and Dihydropyridines |
| URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001200246500001 https://www.ncbi.nlm.nih.gov/pubmed/38598775 |
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