A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles

Gabriella Ieronimo; Giovanni Palmisano; Angelo Maspero; Alessandro Marzorati; Luca Scapinello; Norberto Masciocchi; Giancarlo Cravotto; Alessandro Barge; Marco Simonetti; Keshav Lalit Ameta; Kenneth M. Nicholas; Andrea Penoni

doi:10.1039/C8OB01471J

A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles†‡

Gabriella Ieronimo,^a Giovanni Palmisano,

^a Angelo Maspero,

^a Alessandro Marzorati,^a Luca Scapinello,^a Norberto Masciocchi,

^a Giancarlo Cravotto,

^b Alessandro Barge,

^b Marco Simonetti,^c Keshav Lalit Ameta,

^d Kenneth M. Nicholas

^e and Andrea Penoni

*^a

Author affiliations

* Corresponding authors

^a Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, via Valleggio 9, Como, Italy
E-mail: andrea.penoni@uninsubria.it
Tel: +39 031 2386440

^b Dipartimento di Scienza e Tecnologia del Farmaco, University of Turin, via Pietro Giuria, 9, Turin, Italy

^c School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, United Kingdom

^d Department of Chemistry, College of Arts, Science and Humanities, Mody University of Science and Technology, Lakshmangarh 332311, Rajasthan, India

^e Department of Chemistry and Biochemistry, University of Oklahoma, Stephenson Life Sciences Research Center, 101 Stephenson Parkway, Norman, OK 73019-5251, UK

Abstract

A straightforward indole synthesis via annulation of C-nitrosoaromatics with conjugated terminal alkynones was realised achieving a simple, highly regioselective, atom- and step economical access to 3-aroylindoles in moderate to good yields. Further functionalizations of indole scaffolds were investigated and an easy way to JWH-018, a synthetic cannabinoid, was achieved.

Organic & Biomolecular Chemistry

A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles†‡

Abstract

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A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles

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