Bernard Decroix

BENZOTHIENOINDOLIZIDINES VIA INTRAMOLECULAR ARYL RADICAL CYCLIZATION OR PALLADIUM CATALYZED CYCLIZATION

Indolizidines 4,7 fused to both benzene and thiophene rings were synthesized via intramolecular aryl radical cyclization of enamide 3 or intramolecular Heck reaction of enamidone 5.

A new access to isoindolo[2,1-b][2,4]benzodiazepines through an N-acyliminium ion amide cyclization

Abstract Isoindolo[2,10b][2,4]benzodiazepines 11a–c were synthesized from hydroxylactam-acid 5 when it was treated successively with thionyl chloride, ammonia (or an alkylamine) and p-toluenesulfonic acid.

Acyliminium ion cyclizations: Synthesis of thieno[2′,3′:3,4]pyrrolo[2,1-a] isoindolone and benzo[a]thieno[2,3(3,2 or 3,4)-g]indolizinones

Abstract N-acyliminium cyclizations onto thiophene to give thieno[2′,3′:3,4]pyrrolo[2,1-a]isoindolone (2b) and benzo[a]thieno[2,3(3,2 or 3,4)-g]indolizinones (12a-c) were studied.

Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on π-cationic cyclization

Abstract Chiral pyrroloisothiochroman and pyrrolo[ d ]thiepine were obtained efficiently in four steps from N -alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the N -acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction.

Synthesis of benzo(or furo)[5,6]azepino[2,1-a]isoindolone derivatives: π-cyclisations of N-acyliminium ions

Benzo(or furo)[5,6]azepino[2,1-a]isoindolone and derivatives were obtained easily in one-pot via N-acyliminium ions by treatment of 2-(2-methoxycarbonylbenzyl(or fur-3-yl))phthalimide with alkylmagnesium iodide followed by an acidic hydrolysis.

Heterotricyclic systems: synthesis and reactivity of thieno [2,3(3,2)-b] indolizidin-9-ones

A simple and efficient synthesis of thieno [2,3(3,2)-b] indolizidin-9-ones is described starting from 2(3)-halogenomethylthiophene. The reactivity (Beckmann and Schmidt rearrangements) of these ketones is studied and compared with the reactivity of thienoquinolizidinones and thienoindolizidinediones

Acid-mediated intramolecular cationic cyclization using an oxygen atom as internal nucleophile: synthesis of substituted oxazolo-, oxazino- and oxazepinoisoindolinones ☆ ☆☆

Abstract Efficient assembly of substituted oxazolo-, oxazino-, and oxazepinoisoindolinones ( 5 – 7 , 12 – 15 and 19 ) is described in three steps according to an acidic α-oxoamidoalkylation reaction from ready available phthalic anhydride by successive imidation, sodium borohydride reduction and intramolecular cationic cyclization involving N -acyliminium species. The relative stereochemistry accompanying these reactions was also discussed.

Synthesis of dibenz[c,e]azepine and benzo[e]thieno[c]azepine via, N-acyliminium ion cyclization

Dibenz[c,e]azepine 4a and benzo[e]thieno[c]azepine 4b have been synthesized utilizing the acid-catalyzed cyclization of hydroxylactams 3a,b as key step.

Selective access to N-aryl or N-alkyl derivatives of isoindolo[2,1-b][2,4]benzo(or thieno)diazepines

Abstract N -alkyl isoindolo[2,1-b][2,4]benzodiazepines 15c were synthesized via an intramolecular N -acyliminium ion-amide reaction, N -aryl derivatives 8c were obtained from an intramolecular acylation of amino acids 6c in acetic anhydride. A generalization of these methodologies is given in the synthesis of the thiophenic analogues 15d and 8d .

Synthesis of Phthalimidine-3-carboxylate and Benzopyrroloindolizine from N-(Pyrrol-2-yl) Phthalimidine-3-Carboxylate

Abstract During the synthesis of the new benzo[a]pyrrolo[2,3-f]indolizine system an improved method for the synthesis of phthalimidine-3-carboxylate is reported.