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4-Aminoalkyl Quinolin-2-one Derivatives via Knorr Cyclisation of ω-Amino-β-Keto Anilides
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Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, 70125 Bari, Italy
Department Chemie, Ludwig-Maximilians-Universität München, Butenandstrasse S-13, Haus D, 81377 München, Germany
Authors to whom correspondence should be addressed.
Equally contributing authors.
Academic Editor: Nicholas E. Leadbeater
Molbank 2021, 2021(3), M1267;
Received: 28 June 2021 / Revised: 12 July 2021 / Accepted: 2 August 2021 / Published: 5 August 2021
The lateral metalation-electrophilic trapping reaction of alkyl-substituted pyrazines has always been challenging and poorly regioselective, with the corresponding derivatives often being isolated in moderate yield. In this contribution, we first report on the preparation of an unsymmetrically-substituted pyrazine, that is 2-diphenylphosphinomethyl-3-methylpyrazine, by subjecting to metalation with n-BuLi the commercially available 2,3-dimethylpyrazine, followed by interception of the putative lithiated benzyl-type intermediate with Ph2PCl. Such a functionalization has been successfully carried out in the absence of additional ligands, working either in THF at −78 °C or in a more environmentally friendly solvent like cyclopentyl methyl ether at 0 °C, with the desired phosphine derivative being isolated in 70–85% yield. The newly synthesized adduct has been fully characterized by means of multinuclear magnetic resonance spectroscopic techniques, and also by preparing a selenium derivative, which furnished single crystals that were suitable for X-ray analysis. View Full-Text
Keywords: pyrazines; lithiation; organophosphorus compounds; heterocycles; X-ray diffraction studies; NMR studies pyrazines; lithiation; organophosphorus compounds; heterocycles; X-ray diffraction studies; NMR studies
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MDPI and ACS Style

Boccuzzi, T.; Cicco, L.; Quivelli, A.F.; Vitale, P.; Perna, F.M.; Karaghiosoff, K.; Capriati, V. 2-Diphenylphosphinomethyl-3-methylpyrazine. Molbank 2021, 2021, M1267.

AMA Style

Boccuzzi T, Cicco L, Quivelli AF, Vitale P, Perna FM, Karaghiosoff K, Capriati V. 2-Diphenylphosphinomethyl-3-methylpyrazine. Molbank. 2021; 2021(3):M1267.

Chicago/Turabian Style

Boccuzzi, Tiziana, Luciana Cicco, Andrea F. Quivelli, Paola Vitale, Filippo M. Perna, Konstantin Karaghiosoff, and Vito Capriati. 2021. "2-Diphenylphosphinomethyl-3-methylpyrazine" Molbank 2021, no. 3: M1267.

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