Alessandro Marchesini

Intramolecular Heck reaction of 2- and 3-iodoindole derivatives for the synthesis of β- and γ-carbolinones

A new synthesis of β- and γ-carbolinone derivatives was achieved by an intramolecular Heck cyclisation from the corresponding 3-iodo-1H-indole-2-carboxylic acid allyl-amides 8 and 2-iodo-1H-indole-3-carboxylic acid allyl-amides 9.

Synthesis of [a]annulated carbazoles from indol-2,3-dione

Abstract Reaction of ethyl chloroformate with 3-aroylmethylindol-2(3H)-ones 5 affords the ethyl 3-[(2-aryl-2-ethoxycarbonyloxy)ethenyl]-2-(ethoxycarbonyloxy)indole-1-carboxylates 6 from which the corresponding [a]annulated carbazoles 10 are obtained via 6π-electrocyclization.

An alternative approach to the synthesis of functionalized pyrido[2,3-b]indoles

Abstract A new synthesis of α-carbolines was developed starting from the easily accessible 3-substituted indol-2(3 H )-one derivatives 2 and enamines 3 . The intermediates 4 afforded the α-carbolines 5 and 6 by thermal cyclization with ammonium acetate in glacial acetic acid by way of pyridine ring formation.

A new synthesis of staurosporinone

Abstract A new six steps synthesis of staurosporinone 4, starting from 3-cyano-3-(1H-indol-3-yl)-2-oxo-propionic acid ethyl ester 5, is reported.

Diels-Alder reactions of (Z)-ethyl 3-[(1-ethoxycarbonyloxy-2-methoxy)ethenyl]-2-(ethoxycarbonyloxy)indole-1-carboxylate. Synthesis of the carbazole alkaloid Carbazomycin B

Abstract Diels-Alder reactions of the title 3-vinylindole 2 with N-phenylmaleimide, maleimide, DEAD and DMAD are described. From Compound 10, obtained from 2 and DMAD, Carbazomycin B (1) was prepared.

NEW INDOLE DERIVATIVES. SYNTHESIS OF 3-ACYL-1-CARBETHOXY-2-TRIFLUOROMETHANESULFONYLINDOLES AND OF SUBSTITUTED 2-VINYLINDOLES

Abstract 3-Acyl-1-carbethoxy-2-trifluoromethanesulfonylindoles 6 and 3-acyl-2-vinylindoles 7 are synthesized from 3-[(1-chloro)alkylidene]indol-2(3H)-ones 2 via 1-carbethoxy-3-[(1-dimethylamino)alkylidene]indol-2(3H)-ones 4 .

2-Etboxycarbonyloxy-3-ethynylindoles from indol-2(3H)-ones.

Abstract The treatment of the 3-[(1-chloro-2-substituted)ethylidene]indol-2(3H)-ones 4, prepared from indol-2(3H)-one 1, with ethyl chloroformate and triethylamine gives the ethy 3-(ethynyl)-2-(ethoxy-carbonyloxy)indole-1-carboxylates 7. Some dimeric derivatives of the intermediate allenes have been isolated.

A new synthesis of furostifoline

Abstract Starting from 3-ethoxycarbonylmethyl-indole-1-carboxylic acid ethyl ester 1, a new synthesis of the furo[3,2-a]carbazole furostifoline is reported.

The Vilsmeier-Haack reaction with 3,4-disubstituted isoxazolin-5-ones. A new synthesis of 1,3-oxazin-6-ones and 1,3-oxazine-2,6-diones

Abstract A novel synthesis of 2-dimethylamino-3,4-disubstituted-6 H -1,3-oxazin-6-ones by a Vilsmeier-Haack type reaction on isoxazolin-5-ones is presented.

Synthesis and reactivity of 2-dimethylamino-4-alkenyl-1, 3-oxazin-6-ones

Abstract The Vilsmeier-Haack reaction on 4-alkylideneisoxazolin-5-ones gives 2-dimethylamino-4-alkenyl-1, 3-oxazin-6-ones. Depending on substitution pattern, from these oxazinones, α-pyrones, 2-pyridones and pyridines may be obtained. The results confirm the thermal equilibrium between 2-dialkylamino-1, 3-oxazin-6-ones, iminoketenes and vinylisocyanates.