Synthesis of trans-2-Substituted Cyclopropylamines from α-Chloroaldehydes

Concise synthesis of α-substituted 2-benzofuranmethamines and other 2-subsituted benzofurans via α-substituted 2-benzofuranmethyl carbocation intermediates.

Propargyl amines 4, where R(3) is aryl, undergo 5-exo-dig cyclization reactions under relatively mild conditions (AgNO(3), DMF, 60 °C, 1 h) to give 3-amino-2,3-dihydro-2-arylmethylidenebenzofurans 5 (R(3) = aryl). In contrast, substrates where R(3) is alkyl undergo competing 6-endo-dig and 5-exo-dig cyclization processes. The hydroxymethyl substrate 4 (R(3) = CH(2)OH), however, was smoothly con...

Synthesis and Utilization of α-Substituted Nitroxides

Synthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives.

A comprehensive survey of pathways leading to the generation of α-trifluoromethyl monocyclic piperidinic derivatives is provided (65 references). These compounds have been synthesized either from 6-membered rings e.g., pipecolic acid or lactam derivatives by introduction a trifluoromethyl group, from pyridine or pyridinone derivatives by reduction, and from 5-membered rings e.g., prolinol deriv...

Synthesis and Characterization of 2-(α-p -Substituted phenyl-α-benzimidazolo) methyl benzoxazole

2-p-substituted phenyl-2-benzimidazolo acetonitriles (1a-5a) were prepared by the reaction of benzimidazole , p-substituted benzaldehydes and Sodium cyanide. A series of 2-(α-p -Substituted phenyl-αbenzimidazolo) methyl benzoxazoles (1b-5b) were synthesized by the reaction of 2-p-substituted phenyl-2benzimidazolo acetonitrile(1a-5a) and o-aminophenol in presence of Conc. HCl. These compounds we...

Synthesis of new trans-2-benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones.

The reaction of homophthalic anhydride and N-(furan-2-yl-methylidene)- benzylamine in different solvents and varying temperatures was studied in detail. Mixtures of the expected trans- and cis-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acids trans-5 and cis-5, along with by-products 6 and 7 were obtained in dichloroethane or benzene. In pyridine, used for the first time, the reaction became co...