A highly diastereoselective one-pot three-component 1,3-dipolar cycloaddition of cyclopropenes with azomethine ylides generated from 11H-indeno[1,2-b]-quinoxalin-11-ones

Abstract

A simple and efficient synthesis of compounds with spiro-fused 11H-indeno[1,2-b]quinoxaline and azabicyclo[3.1.0]hexane or cyclopropa[a]pyrrolizine moieties was developed.

Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement: A Theoretical and Experimental Studies

“…It should be noticed that cycloaddition to unsymmetrically substituted isobenzofuran occurs unspecifically and lead to the chromatographically inseparable 1:1 mixture of benzo[h]isoquinolines (Table-1, entries [12][13]. Despite that it crystallizes from ethanol as 2:1 mixture as could be seen by X-ray diffraction analysis from 4-chlorphenyl substituent disorder: 70 % at position 10b benzo[h]isoquinoline structure (according to compound 3l, marked as Cl2 at ORTEP representation) and 30 % at position 6 (compound 4l, marked as Cl3 at ORTEP representation) ( Fig.…”

“…Efficient creation of structural, functional and stereochemical complexity from simple precursors is one of the most desired aspects of new synthetic methodology development. Pericyclic reactions are the powerful tool in organic synthesis and often simplify design complicated heterocyclic natural [1][2][3][4][5][6] and pharmacologically active compounds [7][8][9][10][11][12][13].…”

Synthetic Applications of Cyclopropene and Cyclopropenone: Recent Progress and Developments

“…Among the various available synthetic roots for chiral aminocyclopropane, asymmetric hydroamination of cyclopropene is the most efficient one. [74] Hence, the formation of CÀ N bond has become a promising area of research.…”

An Efficient Regioselective Access to (11Z)‐11‐(3‐Aryl‐5,6‐dihydropyrazin‐2(1H)‐ylidene)‐11H‐indeno[1,2‐b]quinoxaline Derivatives via One‐Pot Three‐Component Reaction

“…11 H ‐Indeno[1,2‐ b ]quinoxalin‐11‐one is a vital family of N ‐heterocycles with four cycles bearing quinoxaline, as well . On the other hand, indenoquinoxaline derivatives have been extensively applied in three‐component reactions for the creation of polycyclic products .…”

“…On the other hand, indenoquinoxaline derivatives have been extensively applied in three‐component reactions for the creation of polycyclic products . Recently, 11 H ‐indeno[1,2‐ b ]quinoxalin‐11‐one derivatives were used as active intermediates in the synthesis of spiro products including spirofuran‐indenoquinoxalines, spiro[benzo[ a ]benz[6,7]chromeno[2,3‐ c ]phenazine] derivatives, spiro‐indenoquinoxaline pyrrolidines, spiro‐indenoquinoxaline pyrrolizidines, spirolactones, and etc …”