Jiaming Liu

Solvent-Free DABCO-Mediated [3 + 2] Cycloadditions of Donor–Acceptor Cyclopropanes with Aldehydes: Strategy for Synthesis of Fully Substituted Furans

DABCO-mediated [3 + 2] cycloadditions of donor-acceptor cyclopropanes with aldehydes under solvent-free conditions have been developed for the preparation of fully substituted furans which are a wide range of structurally interesting and pharmacologically significant compounds. The reaction appears to be general for a variety of 1-cyanocyclopropane-1-carboxylates and aldehydes and tolerates the presence of aromatic moieties with electron-withdrawing and electron-donating substituents.

Four-component reaction between naphthols, substituted β-nitrostyrenes, substituted benzaldehydes and ammonium acetate in water–PEG-400: an approach to construct polysubstituted naphthofuranamines

An eco-friendly straightforward and efficient one-pot four-component protocol has been developed for the synthesis of naphtho[b]furan scaffolds in water–PEG-400 (6:1, v/v) at 80 °C from naphthanols, substituted β-nitrostyrenes, substituted benzaldehydes and ammonium acetate. The new efficient domino reaction formed a furan ring and a Schiff base core by the concomitant formation of C–C, C–O, and C–N multiple bonds presumably involving a sequence of a Michael reaction, aza–ene reaction, imine–enamine/keto–enol tautomerization, O-cyclization and aromatization as key steps.

DBU-mediated [4 + 2] annulations of donor–acceptor cyclopropanes with 3-aryl-2-cyanoacrylates for the synthesis of fully substituted anilines

A facile synthesis of fully substituted anilines by the DBU-mediated [4 + 2] annulation of donor–acceptor 1,1-dicyano-cyclopropanes with 3-aryl-2-cyanoacrylate has been developed. This reaction involves a highly efficient multiple domino sequence consisting of ring opening of donor–acceptor cyclopropanes, regioselective intermolecular Michael addition, intramolecular nucleophilic addition and aromatization as key unit steps. This transformation provides a straightforward synthetic protocol for constructing fully substituted aniline derivatives. The structure of two typical products was confirmed by X-ray crystallography.

Three-component reaction between substituted 2-(2-nitrovinyl)-phenols, acetylenedicarboxylate and amines: diversity-oriented synthesis of novel pyrrolo[3,4- c ]coumarins

An efficient and straightforward synthetic protocol has been developed for the preparation of pyrrolo[3,4-c]coumarins via FeCl3-promoted three component reaction between substituted 2-(2-nitrovinyl)phenols, acetylenedicarboxylate and amines for the generation of a wide range of structurally interesting and pharmacologically significant compounds.

Brönsted acid-mediated annulations of 1-cyanocyclopropane-1-carboxylates with arylhydrazines: efficient strategy for the synthesis of 1,3,5-trisubstituted pyrazoles

1-Cyanocyclopropane-1-carboxylates are reacted with arylhydrazines to afford 1,3,5-trisubstituted pyrazoles under the influence of a Bronsted acid. Formally, this transformation can be regarded as an annulation of three-membered rings with α-carbonyl and hydrazines. This newly efficient method provides access to a variety of structurally diverse pyrazole derivatives. The structures of five typical products were confirmed by X-ray crystallography.

Selective hydrolysis of 1-cyanocyclopropane-1-carboxylates: concise preparation of 1-carbamoylcyclopropane-1-carboxylates

An efficient and straightforward method has been developed for the preparation of 1-carbamoylcyclopropane-1-carboxylate derivatives via selective hydrolysis of 1-cyanocyclopropane-1-carboxylates by using hydroxylamine and sodium acetate system strategy. The structure of 1-carbamoylcyclopropane-1-carboxylate 2a was further confirmed by X-ray single crystal analysis.