DABCO- and DBU-promoted one-pot reaction of N-sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives
In: Beilstein Journal of Organic Chemistry, Jg. 14 (2018), Heft 1, S. 2771-2778
Online
academicJournal
Zugriff:
An intriguing DABCO-catalyzed and DBU-promoted one-pot synthesis of an important class of (2-hydroxyaryl)pyridine derivatives bearing a carboxylate or a nitrile group suitably placed at C3 position of the aza-ring has been achieved in acceptable chemical yields with a broad functional group tolerance. This sequential C–C/C–N bond making process proceeds through a regioselective allylic alkylation/aza-Michael reaction between MBH carbonates derived from an acrylate/acrylonitrile and N-sulfonyl ketimines as C,N-binucleophiles catalyzed by DABCO, followed by elimination of SO2 under the influence of base and subsequent aromatization in an open atmosphere.
Titel: |
DABCO- and DBU-promoted one-pot reaction of N-sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives
|
---|---|
Autor/in / Beteiligte Person: | Guin, Soumitra ; Gupta, Raman ; Majee, Debashis ; Samanta, Sampak |
Link: | |
Zeitschrift: | Beilstein Journal of Organic Chemistry, Jg. 14 (2018), Heft 1, S. 2771-2778 |
Veröffentlichung: | Beilstein-Institut, 2018 |
Medientyp: | academicJournal |
ISSN: | 1860-5397 (print) |
DOI: | 10.3762/bjoc.14.254 |
Schlagwort: |
|
Sonstiges: |
|