Synthesis of polysubstituted fused pyrroles by gold-catalyzed cycloisomerization/1,2-sulfonyl migration of yndiamides
Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolera...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
American Chemical Society
2021
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| _version_ | 1797107410321539072 |
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| author | Smith, PJ Jiang, Y Tong, Z Pickford, HD Christensen, KE Nugent, J Anderson, EA |
| author_facet | Smith, PJ Jiang, Y Tong, Z Pickford, HD Christensen, KE Nugent, J Anderson, EA |
| author_sort | Smith, PJ |
| collection | OXFORD |
| description | Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolerant transformation can be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core. |
| first_indexed | 2024-03-07T07:15:40Z |
| format | Journal article |
| id | oxford-uuid:a3a3c558-6d31-4af3-8d7a-a6b2c66571b4 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:15:40Z |
| publishDate | 2021 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:a3a3c558-6d31-4af3-8d7a-a6b2c66571b42022-08-09T08:14:54ZSynthesis of polysubstituted fused pyrroles by gold-catalyzed cycloisomerization/1,2-sulfonyl migration of yndiamidesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:a3a3c558-6d31-4af3-8d7a-a6b2c66571b4EnglishSymplectic ElementsAmerican Chemical Society2021Smith, PJJiang, YTong, ZPickford, HDChristensen, KENugent, JAnderson, EAYndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolerant transformation can be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core. |
| spellingShingle | Smith, PJ Jiang, Y Tong, Z Pickford, HD Christensen, KE Nugent, J Anderson, EA Synthesis of polysubstituted fused pyrroles by gold-catalyzed cycloisomerization/1,2-sulfonyl migration of yndiamides |
| title | Synthesis of polysubstituted fused pyrroles by gold-catalyzed cycloisomerization/1,2-sulfonyl migration of yndiamides |
| title_full | Synthesis of polysubstituted fused pyrroles by gold-catalyzed cycloisomerization/1,2-sulfonyl migration of yndiamides |
| title_fullStr | Synthesis of polysubstituted fused pyrroles by gold-catalyzed cycloisomerization/1,2-sulfonyl migration of yndiamides |
| title_full_unstemmed | Synthesis of polysubstituted fused pyrroles by gold-catalyzed cycloisomerization/1,2-sulfonyl migration of yndiamides |
| title_short | Synthesis of polysubstituted fused pyrroles by gold-catalyzed cycloisomerization/1,2-sulfonyl migration of yndiamides |
| title_sort | synthesis of polysubstituted fused pyrroles by gold catalyzed cycloisomerization 1 2 sulfonyl migration of yndiamides |
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