One-Pot Knoevenagel and [4 + 2] Cycloaddition as a Platform for Calliviminones

Abstract

Bioactive compounds featuring an unusual core of spiro[5.5]undecenes and calliviminones were synthesized in very good yield with good regio-and diastereoselectivities through a one-pot Knoevenagel and [4 + 2] cycloaddition from the readily available aldehydes, cyclic-1,3-diones, dienes, and a catalytic amount of (S)-proline.

A review of the synthetic strategies toward spirobarbiturate-fused 3- to 7-membered rings

“…As a representative example, 1,3-cyclohexadiene 83 as an adequate diene owing to its cisoid confirmation led to the formation of a bridged spirobarbiturate product with moderate diastereoselectivity of 1.3 : 1 to 3.0 : 1 dr (Scheme 46). 89 In 2021, Yan and co-workers described a CuSO 4 -catalyzed four-component sequential Diels-Alder reaction for the diastereoselective synthesis of functionalized spiro[carbazole-3,5′-pyrimidines].…”

“…As a representative example, 1,3-cyclohexadiene 83 as an adequate diene owing to its cisoid confirmation led to the formation of a bridged spirobarbiturate product with moderate diastereoselectivity of 1.3 : 1 to 3.0 : 1 dr (Scheme 46). 89…”

DABCO-promoted highly diastereo- and regioselective construction of C-3 functionalized spirooxindoles via [3 + 2] cycloaddition of 2-aryl/heteroarylidene-1H-indene-1,3(2H)-diones with N-2,2,2-trifluoroethylisatin ketimines at ambient conditions

“…For the construction of carbon–carbon, carbon–heteroatom bonds, as well as spirocyclic compounds, the 1,3-dipolar cycloaddition reaction has been demonstrated as one of the most fundamental approaches in organic chemistry. 11 Intriguingly, many 1,3-dipoles, including azomethine ylides, 12 nitrones, 13 carbonyl ylides, 14 and others, have been extensively discovered and explored in cycloaddition reactions throughout the past few decades. Among them, recently, N -2,2,2-trifluoroethylisatin ketimines which are easily accessible and highly reactive azomethine ylide precursors 15 have been successfully employed in many 1,3-dipolar cycloadditions with various activated olefins and has been demonstrated as one of the efficient approaches for the stereoselective construction of spiro-pyrrolidine oxindoles.…”

Microwave-assisted catalyst-free multicomponent one-pot green synthesis of highly functionalized aminocyanopyridines and (4-hydroxy)quinolines in aqueous medium and its in silico studies

“…1 compound III ) which is a building block of various carbazolespirooxindoles or quaternary carbon stereocenters which are interesting targets for medicinal research and many other synthetic applications. 32,51–60…”

“…1 compound III) which is a building block of various carbazolespirooxindoles or quaternary carbon stereocenters which are interesting targets for medicinal research and many other synthetic applications. 32,[51][52][53][54][55][56][57][58][59][60] Moreover, in order to determine the binding mechanism and fate of synthesized compounds, we have employed molecular modelling studies with mitogen-activated protein kinaseactivated protein kinase 2 which is effective in the treatment of diseases like rheumatoid and psoriatic arthritis. 24 Molecular docking analyses are widely used to illustrate the binding mechanism of drugs with their specific protein target for different diseases.…”