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Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction.
J Org Chem
August 2024
College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing -hydroxyphenyl group. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 3-(-hydroxyarylidene)indolin-2-ones in tetrahydrofuran at 60 °C resulted in unique functionalized spiro[cyclobuta[]chromene-1,3'-indolines] in good yields and with high diastereoselectivity. However, the similar three-component reaction with 2-(5-halo-2-hydroxyarylidene)indolin-2-ones afforded unexpected chain products in satisfactory yields.
View Article and Find Full Text PDFConstruction of Unique Spiro[dibenzo[,]azulene-6,2'-indenes] via Unprecedented Annulation of -C-H Bond of Benzylidene Group.
J Org Chem
November 2023
College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
The domino reaction of alkyl and aryl isocyanides with two molecules of 2-arylidene-1,3-indanediones in acetonitrile at 80 °C resulted in unique functionalized spiro[dibenzo[,]azulene-6,2'-indenes] in good yields, in which the two 2-arylidene-1,3-indanediones acted as different building blocks to construct the polycyclic system. More importantly, the unprecedented anticipation of the ortho-position of benzylidene group to form a novel dibenzo[,]azulene ring through a formal [5 + 2] cycloaddition process was first observed. On the other hand, DABCO-promoted reaction of the isocyanides with two molecules of 2-arylidene-1,3-indanediones in acetonitrile at 80 °C afforded functionalized spiro[cyclopenta[]-indene-2,2'-indene] derivatives.
View Article and Find Full Text PDFEnantioselective Synthesis of Bispiro[indanedione-oxindole-cyclopropane]s through Organocatalytic [2+1] Cycloaddition.
J Org Chem
June 2023
School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, China.
A series of compounds featuring a novel bispiro[indanedione-oxindole-cyclopropane] moiety have been synthesized through a squaramide-catalyzed [2+1] cycloaddition reaction. The tandem Michael-alkylation reaction of 2-arylidene-1,3-indanediones with 3-bromooxindoles furnished the cycloadducts in high yields with excellent diastereo- and enantioselectivities. The ammonium ylide in the catalytic process, as a key intermediate, was revealed by the high-resolution mass spectrometry study.
View Article and Find Full Text PDFSelective Construction of Diverse Polycyclic Spirooxindoles via a Three-Component Reaction of Cyclic Mercapto-Substituted β-Enamino Esters, Isatins, and Cyclic 1,3-Diketones.
J Org Chem
October 2020
College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
The three-component reaction of alkyl 2-(benzo[][1,4]thiazin-3-ylidene)acetates, isatins, and 1,3-indanedione (1,3-cyclopentanedione) in ethanol in the presence of acetic acid conveniently afforded spiro[indeno[1,2-]phenothiazine-6,3'-indolines] or spiro[cyclopenta[]phenothiazine-4,3'-indolines] in good yields and with high diastereoselectivity. More interestingly, a similar three-component reaction with 4-hydroxychromen-2-one resulted in the unexpected polycyclic spiro[benzo[]chromeno[3',4':5,6]pyrano[2,3-][1,4]thiazine-7,3'-indolines] in satisfactory yields. A plausible reaction mechanism was rationally proposed for formation of different kinds of the spiro compounds, and the stereochemistries of the various spiro compounds were clearly elucidated.
View Article and Find Full Text PDFConstruction of Dispiro-Indenone Scaffolds via Domino Cycloaddition Reactions of α,β-Unsaturated Aldimines with 2-Arylidene-1,3-indenediones and 2,2'-(Arylmethylene)bis(1,3-indenediones).
ACS Omega
August 2019
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
The catalyst-free domino reaction of α,β-unsaturated -alkyl or -arylaldimines with two molecules of 2-arylidene-1,3-indanediones in dry acetonitrile resulted in polysubstituted spiro[indene-2,3'-indeno[2',1':5,6]pyrano[2,3-]pyridines] in moderate to good yields and with high diastereoselectivity. The reaction mechanism included sequential aza/oxa-Diels-Alder reactions via both endo-transition states. On the other hand, the catalyst-free domino reaction of α,β-unsaturated -arylaldimines with 2,2'-(arylmethylene)bis(1,3-indenediones) afforded the mixed diastereoisomeric dispiro[indene-2,1'-cyclohexane-3',2″-indene] derivatives in satisfactory yields.
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