Further Developments on the Regioselective Synthesis of 3-Aroylindole Derivatives from <i>C</i>-Nitrosoaromatics and Alkynones: A Novel Synthetic Approach to Pravadoline, JWH-073, Indothiazinone Analogues and Related Compounds — Oak Academic Publishing
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Further Developments on the Regioselective Synthesis of 3-Aroylindole Derivatives from <i>C</i>-Nitrosoaromatics and Alkynones: A Novel Synthetic Approach to Pravadoline, JWH-073, Indothiazinone Analogues and Related Compounds
Department of Science and High Technology, University of Insubria, Como, Italy
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Department of Science and High Technology, University of Insubria, Como, Italy
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Department of Science and High Technology, University of Insubria, Como, Italy
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Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, India
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Department of Drug Science and Technology, University of Turin, Turin, Italy
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School of Chemistry, University of Manchester, Manchester, UK
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Department of Science and High Technology, University of Insubria, Como, Italy
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Department of Science and High Technology, University of Insubria, Como, Italy
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Stephenson Life Sciences Research Center, Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK, USA
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Department of Science and High Technology, University of Insubria, Como, Italy
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Department of Science and High Technology, University of Insubria, Como, Italy
1 Department of Science and High Technology, University of Insubria, Como, Italy
2 Department of Science and High Technology, University of Insubria, Como, Italy
3 Department of Science and High Technology, University of Insubria, Como, Italy
4 Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, India
5 Department of Drug Science and Technology, University of Turin, Turin, Italy
6 School of Chemistry, University of Manchester, Manchester, UK
7 Department of Science and High Technology, University of Insubria, Como, Italy
8 Department of Science and High Technology, University of Insubria, Como, Italy
9 Stephenson Life Sciences Research Center, Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK, USA
10 Department of Science and High Technology, University of Insubria, Como, Italy
11 Department of Science and High Technology, University of Insubria, Como, Italy
An uncatalyzed and easily accessible synthetic approach for the preparation of 3-aroylindoles was investigated using nitrosoarenes and aromatic terminal ethynyl ketones. Indole derivatives were produced in good yields and excellent regioselectivity. Functionalizations of the indole products were carried out affording highly valuable and versatile compounds. The indolization protocol was studied as a fundamental step for the preparation of pravadoline and 1-butyl-3-(1-naphthoyl)indole (JWH-073), bioactive molecules showing antinociceptic properties.
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