DABCO-Promoted Cyclization of 2-Amino-4H-chromen-4-ones with 2,6-Dibenzylidenecyclohexan-1-ones for the Synthesis of Chromeno[2,3-b]tetrahydroquinoline.

DABCO-promoted cyclization reaction of substituted 2-amino-4H-chromen-4-ones with substituted 2,6-dibenzylidenecyclohexan-1-ones was investigated under mild conditions. This reaction provided a novel and efficient access to the 7,8,9,10-tetrahydro-12H-chromeno[2,3-b]quinolin-12-ones in good yields, the exocyclic double bond of which is predominantly E-selective.

Piperidine-Mediated [3 + 3] Cyclization of 2-Amino-4H-chromen-4-ones and 2-Benzylidenemalononitriles: To Access 2-Aminochromeno[2,3-b]pyridine Derivatives.

Piperidine-mediated [3 + 3] cyclization of 2-amino-4H-chromen-4-ones and substituted 2-benzylidenemalononitriles was developed for the synthesis of 2-amino-4-aryl-5H-chromeno[2,3-b]pyridin-5-one derivatives. This novel transformation provides a highly efficient and facile route to functionalized 5H-chromeno[2,3-b]pyridines from readily available substrates under mild reaction conditions.

DBU-promoted ring-opening reactions of multi-substituted donor-acceptor cyclopropanes: access to functionalized chalcones with a quaternary carbon group.

A convenient and straightforward strategy to synthesize Z-configuration chalcones with alkylcyanoacetate subunits via DBU-promoted ring-opening reactions of multi-substituted D-A cyclopropanes has been developed. This reaction did not require a transition metal catalyst and extra solvent, and haloalkanes acted as both an alkylation reagent and solvent.

DBU-Promoted Cascade Selective Nucleophilic Addition/C-C Bond Cleavage/Hetero-Diels-Alder Reactions of 2-Amino-4H-chromen-4-ones with ß-Nitrostyrenes and/or Aryl Aldehydes: Access to 5H-Chromeno[2,3-b]pyridin-5-ones.

DBU-promoted cascade selective nucleophilic addition/C-C bond cleavage/hetero-Diels-Alder reactions accompanied by aromatization of substituted 2-amino-4H-chromen-4-ones with substituted ß-nitrostyrenes or with the combined substituted ß-nitrostyrenes and aromatic aldehydes were developed for the synthesis of 2,4-diaryl-substituted 5H-chromeno[2,3-b]pyridin-5-ones. This procedure provides a highly efficient and facile route to functionalized 5H-chromeno[2,3-b]pyridines from readily available substrates under mild reaction conditions.

DBU-mediated annulation of 2-aryl-3-nitro-2H-chromenes with 1,3-cyclohexanediones for the synthesis of benzofuro[2,3-c]chromenone derivatives.

The DBU-mediated annulations of 2-aryl-3-nitro-2H-chromenes with 1,3-cyclohexanediones have been developed. This reaction involves a highly efficient domino sequence consisting of regioselective intermolecular Michael addition, intramolecular nucleophilic addition and aromatization as key unit steps. The reaction appears to be general for a variety of 2-aryl-3-nitro-2H-chromenes and tolerates the presence of aromatic moieties with electron-withdrawing and electron-donating substituents. This transformation provides a straightforward synthetic protocol for constructing benzofuro[2,3-c]chromenone derivatives.

Direct synthesis of highly functionalized furans from donor-acceptor cyclopropanes via DBU-mediated ring expansion reactions.

A DBU-mediated, unprecedented formal ring expansion reaction of 2-acyl-3-arylcyclopropane-1,1-dicarbonitriles for the synthesis of multisubstituted furan derivatives is reported. This transformation represents the regioselective ring-opening reaction of cyclopropane-1,1-dicarbonitriles and annulation using an intramolecular addition cascade reaction protocol for the synthesis of fully substituted furans includes use of readily available starting materials, mild reaction conditions, and it is transition-metal catalyst free, has good functional tolerance, and broad substrate scope.

DBU-Mediated Cyclization of Acylcyclopropanecarboxylates with Amidines: Access to Polysubstituted Pyrimidines.

DBU-mediated cyclization of 2-acyl-1-cyanocyclopropanecarboxylates with amidines for the synthesis of multisubstituted pyrimidine derivatives is described. This reaction gives a practical method for producing a diverse set of pyrimidines, having simple experimentation, readily available starting materials, a wide substrate scope, and very good yields.

Cesium-Carbonate-Mediated Benzalation of Substituted 2-Aryl-3-nitro-2 H-chromenes with Substituted 4-Benzylidene-2-phenyloxazol-5(4 H)-ones.

Cs2CO3-mediated domino benzalation reaction with a variety of 2-aryl-3-nitro-2 H-chromenes and 4-benzylidene-2-phenyloxazol-5(4 H)-ones has been realized. The reaction proceeds smoothly with a broad substrate scope, thus providing a variety of substituted ( Z)-4-(( Z)-benzylidene)chroman-3-one oximes in moderate to high yields, which were easily transformed into biologically important 4 H-chromeno[3,4- c]isoxazoles.

DBU-Promoted Cascade Annulation of Nitroarylcyclopropane-1,1-dicarbonitriles and 3-Aryl-2-cyanoacrylates: An Access to Highly Functionalized Cyclopenta[ b]furan Derivatives.

A DBU-promoted cascade annulation of nitroarylcyclopropane-1,1-dicarbonitriles and 3-aryl-2-cyanoacrylates for the synthesis of highly functionalized cyclopenta[ b]furan derivatives is described. High stereoselectivity, fused cyclopentane and furan can be established in a single reaction, highlighting the high efficiency and step-economy of this protocol. This reaction offers a novel and straightforward protocol to the synthesis of cyclopenta[ b]furans featuring the [3 + 2] cycloadditions of nitroarylcyclopropane-1,1-dicarbonitriles with 3-aryl-2-cyanoacrylates.