Application of the intramolecular Diels-Alder vinylarene (IMDAV) reaction for the synthesis of benzo-, carbocyclo-, thienothiopheneisoindolecarboxylic acids and its limitations.

Thienylallylamines, readily accessible from the corresponding thienyl aldehydes, react with maleic and trifluoromethylmaleic anhydrides leading to the formation of acids with a thieno[2,3-]isoindole core. The reaction sequence involves two successive steps: acylation of the nitrogen atom of the initial allylamine and the intramolecular Diels-Alder vinylarene (IMDAV) reaction. The scope and limitations of the proposed method were thoroughly investigated.

Domino Three-Component -Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[]isoindole-4-carboxylic Acids.

Diversely substituted, partially saturated benzo[]isoindole-4-carboxylic acids were synthesized by a new three-component reaction (3CR) starting from cinnamic amines (3-arylallylamines), maleimides, and maleic anhydride. The process consists of -acylation of the amines by maleic anhydride, intramolecular [4 + 2] cycloaddition in vinylarenes (the IMDAV reaction), and the concluding Alder-ene reaction between Diels-Alder intermediates and maleimides. All of the reaction steps proceed in a highly regio- and stereoselective manner, furnishing five adjacent chiral centers and leading to a single diastereoisomer of the title compound.

Crystal structure and Hirshfeld surface analysis of ()-3-hy-droxy-2-{[(3a,6,7a)-2-(4-methyl-phenyl-sulfon-yl)-2,3,3a,6,7,7a-hexa-hydro-3a,6-ep-oxy-1-isoindol-6-yl]meth-yl}isoindolin-1-one.

The title compound, CHNOS, crystallizes with two independent mol-ecules ( and ) in the asymmetric unit. In the central ring systems of both mol-ecules, the tetra-hydro-furan rings adopt envelope conformations, the pyrrolidine rings adopt a twisted-envelope conformation and the six-membered ring is in a boat conformation. In mol-ecules and , the nine-membered groups attached to the central ring system are essentially planar (r.

Crystal structure and Hirshfeld surface analysis of 4,5-di-bromo-6-methyl-2-phenyl-2,3,3a,4,5,6,7,7a-octa-hydro-3a,6-ep-oxy-1-isoindol-1-one.

In the title compound, CHBrNO, two bridged tetra-hydro-furan rings adopt envelope conformations with the O atom as the flap. The pyrrolidine ring also adopts an envelope conformation with the spiro C atom as the flap. In the crystal, the mol-ecules are linked into dimers by pairs of C-H⋯O hydrogen bonds, thus generating (18) rings.

IMDAV reaction between phenyl-maleic anhydride and thien-yl(fur-yl)allyl-amines: synthesis and mol-ecular structure of (3a,4,4a,7a)-5-oxothieno- and (3a,4,4a,7a)-5-oxofuro[2,3-]iso-indole-4-carb-oxy-lic acids.

The title compounds CHNOS, , and CHNO, , are the products of the IMDAV reaction between phenyl-maleic anhydride and thien-yl(fur-yl)allyl-amines. Their mol-ecular structures comprise fused tricyclic systems containing thio-phene, cyclo-hexene and pyrrolidine rings () or furan, cyclo-hexene and pyrrolidine rings (). The central cyclo-hexene and pyrrolidine rings in both compounds adopt slightly twisted boat and envelope conformations, respectively.