Ru-Catalyzed Regioselective Cascade Annulation of Acrylamides with 2-Alkynoates for the Synthesis of Various 6-Oxo Nicotinic Acid Esters
作者:Dnyaneshwar N. Garad、Santosh B. Mhaske
DOI:10.1021/acs.joc.8b02783
日期:2019.2.15
of acrylamides with 2-alkynoates via aza-Michael/C–H activation sequence for the synthesis of various 6-oxo nicotinicacidesters is described. The regioselectivity of the protocol has been confirmed by performing silver mediated protodecarboxylation of the corresponding 6-oxo nicotinicacid to furnish 2-pyridone. The developed protocol is copper or silver salt-free and uses inexpensive, safe, and
α,β-Unsaturated acids, through their acid chlorides, react with tritylamine in the presence of triethylamine under mild conditions, to afford in high yield and high regioselectivity the corresponding β,γ-unsaturated tritylamides. Detritylation with TFA generates quantitatively β,γ-unsaturated primary amides. An investigation of this deconjugative isomerization was performed.
Cross-Coupling of Acrylamides and Maleimides under Rhodium Catalysis: Controlled Olefin Migration
作者:Satyasheel Sharma、Sang Hoon Han、Yongguk Oh、Neeraj Kumar Mishra、Suk Hun Lee、Joa Sub Oh、In Su Kim
DOI:10.1021/acs.orglett.6b00909
日期:2016.6.3
The rhodium(III)-catalyzed direct cross-coupling reaction of electron-deficient acrylamides with maleimides is described. This protocol displays broad functional group tolerance and high efficiency, which offers a new opportunity to access highly substituted succinimides. Dependent on the substituent positions of acrylamides and reaction conditions, olefin migrated products were obtained with high
1,4-Addition of RLi, RMgX, and (RS) 2CHLi reagents to unsaturatedamides 2a-c followed by α-alkylation is shown to constitute a general and efficient synthetic procedure for the formation of two CC bonds in a single step.