21505-28-2Relevant academic research and scientific papers
Catalytic multicomponent reactions for the synthesis of N-aryl trisubstituted pyrroles
Galliford, Chris V.,Scheldt, Karl A.
, p. 1811 - 1813 (2007)
Dirhodium(II) salts efficiently catalyze the three-component assembly reaction of an imine, diazoacetonitrile (DAN), and an activated alkynyl coupling partner to form substituted 1,2-diarylpyrroles in moderate to good yields. The transition-metal-catalyze
An efficient and convenient synthesis of 4-polyfluoroalkylated pyrrole-3-carboxylates through 1,3-dipolar cycloaddition reaction of polyfluoro-2-alkynoic acid esters with munchnones
Funabiki, Kazumasa,Ishihara, Takashi,Yamanaka, Hiroki
, p. 5 - 8 (1995)
1,3-Dipolar cycloaddition between polyfluoro-2-alkynoic acid esters and 1,3-oxazolium 5-olates (munchnones) readily proceeds in a regiospecific manner under very mild reaction conditions, followed by simultaneous decarboxylation to afford 4-(polyfluoroalk
The first example of the generation of azomethine ylides from a fluorocarbene: 1,3-Cyclization and 1,3-dipolar cycloaddition
Konev, Alexander S.,Novikov, Mikhail S.,Khlebnikov, Alexander F.
, p. 8337 - 8340 (2005)
The reaction of Schiff bases with fluorocarbene, generated by reduction of dibromofluoromethane with active lead in the presence of Bu4NBr under ultrasound irradiation, involves the formation of fluoro-substituted azomethine ylides which undergo cyclization into aziridines. 1,3-Cyclization of ylides, generated from N-arylimines of benzaldehyde, proceeds stereoselectively. When carrying out the reaction of Schiff bases with fluorocarbene in the presence of dimethyl maleate or dimethyl acetylenedicarboxylate, the products of dehydrofluorination of the primary adducts of the 1,3-dipolar cycloaddition of fluoro-substituted azomethine ylides to multiple bonds of dipolarophiles were obtained. In the case of the reaction of N-alkylimines of benzaldehyde the cycloaddition of ylides to dimethyl maleate completely suppressed the cyclization to aziridines.
Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines
Konev,Novikov,Khlebnikov
, p. 286 - 296 (2007/10/03)
N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-π-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dimethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-π-cyclization, in the presence of acid catalysts suffer isomerization into α-fluoroimines and 1,3-disubstituted indoles.
ADDITION OF α-HALOSULFINYL BARBANIONS TO IMINES. CONVENIENT PREPARATIONS OF SUBSTITUTED AZIRIDINES AND PYROLES
Mahidol, Chulabhorn,Reutrakul, Vichai,Prapansiri, Vichukorn,Panyachotipun, Chitchaun
, p. 969 - 972 (2007/10/02)
α-Lithio-α-chloro and -α-fluoromethyl phenyl sulfoxides react with N-(benzylidene)anilines to give the corresponding aziridines in good yields.Pyrolyses of these compounds in the presence of dimethyl acetylenedicarboxylate result in substituted pyrroles in high yields.
A NEW METHOD FOR THE SYNTHESIS OF 2-PHENYLSULFONYLAZIRIDINES VIA THE REACTION OF α-HALOSULFONYL CARBANION TO IMINES
Reutrakul, Vichai,Prapansiri, Vichukorn,Panyachotipun, Chitchanun
, p. 1949 - 1952 (2007/10/02)
The reaction of lithio α-chloromethyl phenyl sulfone with imines gave aziridines in good yields.The resulting aziridines were alkylated and underwent the 1,3-dipolar cycloaddition with dimethylacetylene dicarboxylate to give pyrroles in excellent yields.
