A New, Simple, and High-Yielding Synthesis of 2,9-Dihydro-1H-pyrido[3,4-b]indol-1-ones

Giuseppe La Regina; Valeria Famiglini; Sara Passacantilli; Sveva Pelliccia; Pasqualina Punzi; Romano Silvestri

doi:10.1055/s-0033-1339155

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(15): 2093-2097
DOI: 10.1055/s-0033-1339155

paper

A New, Simple, and High-Yielding Synthesis of 2,9-Dihydro-1H-pyrido[3,4-b]indol-1-ones

Giuseppe La Regina*

^aIstituto Pasteur - Fondazione Cenci Bolognetti, Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Piazzale Aldo Moro 5, 00185 Rome, Italy Fax: +39(06)49913993 eMail: giuseppe.laregina@uniroma1.it

,

Valeria Famiglini

^aIstituto Pasteur - Fondazione Cenci Bolognetti, Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Piazzale Aldo Moro 5, 00185 Rome, Italy Fax: +39(06)49913993 eMail: giuseppe.laregina@uniroma1.it

,

Sara Passacantilli

^aIstituto Pasteur - Fondazione Cenci Bolognetti, Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Piazzale Aldo Moro 5, 00185 Rome, Italy Fax: +39(06)49913993 eMail: giuseppe.laregina@uniroma1.it

,

Sveva Pelliccia

^bDipartimento di Farmacia, Università di Napoli Federico II, Via Domenico Montesano 49, 80131 Naples, Italy

,

Pasqualina Punzi

^cDipartimento di Chimica, Sapienza Università di Roma, Piazzale Aldo Moro 5, 00185 Rome, Italy

,

Romano Silvestri

^aIstituto Pasteur - Fondazione Cenci Bolognetti, Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Piazzale Aldo Moro 5, 00185 Rome, Italy Fax: +39(06)49913993 eMail: giuseppe.laregina@uniroma1.it

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Abstract

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Abstract

A new, simple, and high-yielding method was developed to prepare 2,9-dihydro-1H-pyrido[3,4-b]indol-1-ones by selective cyclization of the appropriate N-(2,2-dimethoxyethyl)-1H-indole-2-carboxamide in polyphosphoric acid at 110 °C for 30 minutes. The reaction yield was strongly dependent on the acid used. The method was less affected by the presence of electron-donating and -withdrawing substituents at 5-position of the indole nucleus.

Key words

β-carbolinones - β-carboline - polyphosphoric acid - cyclization - heterocycles

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Referenzen

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