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Synthesis 2014; 46(15): 2093-2097
DOI: 10.1055/s-0033-1339155
paper
© Georg Thieme Verlag Stuttgart · New York

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

Giuseppe La Regina*
a   Istituto 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
a   Istituto 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
a   Istituto 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
b   Dipartimento di Farmacia, Università di Napoli Federico II, Via Domenico Montesano 49, 80131 Naples, Italy
,
Pasqualina Punzi
c   Dipartimento di Chimica, Sapienza Università di Roma, Piazzale Aldo Moro 5, 00185 Rome, Italy
,
Romano Silvestri
a   Istituto 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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Publikationsverlauf

Received: 29. November 2013

Accepted after revision: 10. Mai 2014

Publikationsdatum:
02. Juni 2014 (online)

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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

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084. Included are copies of 1H NMR, 13C NMR and HRMS spectra of compounds 5–11.
  • Supporting Information
 

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