Comprehensive SummaryA highly selective palladium-catalyzed carbonylation of 2-alkynylanilines bearing an amide moiety to condensed six-membered heterocyclic structures has been developed under mild conditions (room temperature and atmospheric pressure of CO). The carbonylative protocol is also compatible with CO surrogates, such as benzene-1,3,5-triyl triformate (TFBen) or the newly developed calix[6]arenes functionalized with six formate groups (CLX[6]CO), which are both capable to release CO in situ. A series of tricyclic fused heterocycles containing the important oxazino-quinolinone scaffold have been selectively obtained (only the 6-endo-dig cyclization mode has been observed) in good to excellent yields (up to 99%).

Palladium-Catalyzed Carbonylation of Multifunctionalized Substituted Alkynes to Quinolinone Derivatives under Mild Conditions† / Voronov, A.; Pancrazzi, F.; Constantin, A. M.; Maggi, R.; Mancuso, R.; Gabriele, B.; Olivieri, D.; Carfagna, C.; Casnati, A.; Rispoli, F.; Baldini, L.; Della Ca', N.. - In: CHINESE JOURNAL OF CHEMISTRY. - ISSN 1001-604X. - 41:23(2023), pp. 3223-3228. [10.1002/cjoc.202300337]

Palladium-Catalyzed Carbonylation of Multifunctionalized Substituted Alkynes to Quinolinone Derivatives under Mild Conditions†

Voronov A.;Pancrazzi F.;Constantin A. M.;Maggi R.;Casnati A.;Rispoli F.;Baldini L.;Della Ca' N.
2023-01-01

Abstract

Comprehensive SummaryA highly selective palladium-catalyzed carbonylation of 2-alkynylanilines bearing an amide moiety to condensed six-membered heterocyclic structures has been developed under mild conditions (room temperature and atmospheric pressure of CO). The carbonylative protocol is also compatible with CO surrogates, such as benzene-1,3,5-triyl triformate (TFBen) or the newly developed calix[6]arenes functionalized with six formate groups (CLX[6]CO), which are both capable to release CO in situ. A series of tricyclic fused heterocycles containing the important oxazino-quinolinone scaffold have been selectively obtained (only the 6-endo-dig cyclization mode has been observed) in good to excellent yields (up to 99%).
2023
Palladium-Catalyzed Carbonylation of Multifunctionalized Substituted Alkynes to Quinolinone Derivatives under Mild Conditions† / Voronov, A.; Pancrazzi, F.; Constantin, A. M.; Maggi, R.; Mancuso, R.; Gabriele, B.; Olivieri, D.; Carfagna, C.; Casnati, A.; Rispoli, F.; Baldini, L.; Della Ca', N.. - In: CHINESE JOURNAL OF CHEMISTRY. - ISSN 1001-604X. - 41:23(2023), pp. 3223-3228. [10.1002/cjoc.202300337]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2982294
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