Michel Farnier

A general method for the synthesis of 2-arylpyrroles

Abstract Reaction of methyl azidoacetate with β-arylacroleins, followed by cyclisation of the obtained derivatives easily leads to arylpyrroles. N M R and mass spectra data are given and the Vilsmeier formylation of some arylpyrroles is described.

Reactivity of iminophosphoranes towards some symmetrical dicarbonyl dichlorides : syntheses and mechanisms

Abstract In situ generated iminophosphoranes 1 react with dicarbonyl dihalides 2a-b and 3a-c to give known or new nitrogen heterocycles. The proposed mechanisms involve elimination of either triphenyl-phosphine oxide or dichlorotriphenylphosphorane depending upon both the iminophosphorane and the dicarbonyl compound.

Synthesis of dipyrazolo[3,4-b : 4′,3′-f]azepines and dithieno[2,3-b : 3′,2′f]azepines from 1-substituted 2,7-dichloro-4,5-dihydro-1H-azepine-3,6-dicarbaldehydes

Syntheses of the title compounds (7) and (8) are described. These new bis-heterocyclic analogues of dibenzo[b,f]azepines (4) were readily obtained from the di-β-chlorovinyl aldehydes (3), the latter prepared by formylation of the azepines (5). The thiophene analogue (10) of the antidepressant ‘imipramine’ was then synthesized by debenzylation of the dithienoazepine (8a) followed by condensation with an appropriate halide.

New cyclopenta [b]-pyrroles and -pyridines by reaction of 2-azido- and 2-phosphoranylideneaminocyclopent-1-ene-1-carbaldehydes with aliphatic esters

A new cyclopenta [b]pyrrole has been synthesized by reaction of 2-azidocyclopent-1-ene-1-carbaldehyde with ethyl acetate and subsequent thermal cyclisation. Dicyclopenta [b,e] pyrazines have been isolated from a similar reaction with ethyl propionate or t-butyl propionate. Condensation of the corresponding iminophosphorane from 2-azidocyclopent-1-ene-1-carbaldehyde with ethyl acetate and cyclisation of the dienic iminophosphorane so obtained gave a cyclopenta[b]pyridine. The products were characterized on the basis of 1H n.m.r., i.r., and mass spectrometric results.

Synthesis and characterization of bis(phenyltetrazolato)-germanium(IV) and -tin(IV) porphyrins

Bis(phenyltetrazolato)-germanium(IV) and -tin(IV) metalloporphyrins have been synthesized by the action of benzonitrile on diazido-germanium(IV) and -tin(IV) porphyrins. The structure of the complexes studied has been demonstrated on the basis of elemental analysis, mass spectrometry, 1H n.m.r., i.r., and u.v.–visible spectroscopy.