Jean Guillaumel

Sur la transformation du β-nitrostyrène sous l'action du chlorure d'acétyle en présence d'un chlorure métallique

Abstract While β-nitrostyrene yields only hydroxymic or hydroxamic acid derivatives by treatment with acetyl chloride in the presence of zinc, tin, titanium or aluminium chloride, it also gives 3-chloro 2-indolinone and a 5-acetyl derivative of the latter, when the reaction is carried out with ferric chloride. The procedures of this reaction are examined, and a mechanism is suggested.

Synthesis and antiproliferative activity of basic ethers of 1,2-dihydropyrrolo[1,2-a]indole, 6H-isoindolo[2,1-a]indole, and 6H-benz[5,6]isoindolo[2,1-a]indole.

Monobasic ethers of 1,2-dihydropyrrolo[1,2-a]indole, 6H-isoindolo[2,1-a]indole, and 6H-benz[5,6]isoindolo[2,1-a]indole and bis-basic ethers of 6H-isoindolo[2,1-a]indole were prepared using an intramolecular Wittig cyclization as a key step. All these compounds were firstly evaluated for their cytotoxicity effects against L1210 cell line. Only the tetracyclic bis-basic ether 14d displayed submicromolar cytotoxic effect. Moreover, despite the fact that the presence of these two amino side chains in 14c, 14d, and 14f led to strong DNA binding effect, they are not topoisomerase II inhibitors. Among the monobasic ethers 14a, 14b, 22, and 29, which do not bind to DNA, the pentacyclic analog 29 exhibited micromolar cytotoxic activity against L1210 and HT-29 cell lines and induced a weak topoisomerase II inhibition.

Sur une transformation inhabituelle de nitro-2 benzofurannes dans les conditions de la reaction de friedel et crafts

Abstract On treatment with acetyl chloride or acetic anhydride in presence of aluminium chloride in methylene chloride. 2-nitro and 5-chloro 2-nitro benzofurans yield 2,3-dichloro benzofurans, 3-chloro 2-coumaranones and 2-acetoximino 3-chloro coumarans. By the action of acetyl chloride, in presence of titanium (IV) chloride in methylene chloride, on 2-nitro benzofuran, 2,3-dichloro benzofuran can be obtained with a fairly good yield beside a relatively restricted quantity of 3-chloro 2-coumaranone. In the same conditions, 5-chloro-2-nitro benzofuran yields not only 2,3,5-trichloro benzofuran but also 2,2,3,3,5-pentachloro coumaran and, occasionally. 3,5-dichloro 2-coumaranone.

Sur une transformation inattendue du β-methyl β-nitrostyrene en aldehyde salicylique

Abstract An unexpected route to o-hydroxybenzaldehyde is described. Thus, β-methyl β-nitrostyrene mixed with acetyl chloride and aluminium chloride at 0° yields upto 45% salicylaldehyde besides 2-acetoximino 1-chloro 1-phenyl propane and dichloromethyl benzene as minor products.

An unexpected rearrangement of 2-(2-benzofuranyl)-benzonitriles: a new route to phenylmethylene-dihydro-isoindolinones

Depending on the solvent used, the alkaline hydrolysis of 2-(2-benzofuranyl)-benzonitriles leads to the expected amide or acid, or to isoindolinones by rearrangement.