Rearrangement of 7-Aryloxazolo[5,4- b]pyridines to Benzo[ c][1,7]naphthyridine-4(3 H)-ones and Thieno[3,2- c][1,7]naphthyridine-6(7 H)-ones

Anton L Shatsauskas; Tatyana E Mamonova; Anton J Stasyuk; Sergey A Chernenko; Pavel A Slepukhin; Anastasia S Kostyuchenko; Alexander S Fisyuk

doi:10.1021/acs.joc.0c01299

Rearrangement of 7-Aryloxazolo[5,4- b]pyridines to Benzo[ c][1,7]naphthyridine-4(3 H)-ones and Thieno[3,2- c][1,7]naphthyridine-6(7 H)-ones

J Org Chem. 2020 Aug 7;85(15):10072-10082. doi: 10.1021/acs.joc.0c01299. Epub 2020 Jul 21.

Authors

Anton L Shatsauskas¹, Tatyana E Mamonova², Anton J Stasyuk³, Sergey A Chernenko¹, Pavel A Slepukhin⁴, Anastasia S Kostyuchenko^{1

2}, Alexander S Fisyuk¹

Affiliations

¹ Laboratory of New Organic Materials, Omsk State Technical University, Mira Avenue, 11, 644050 Omsk, Russia.
² Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Avenue, 55a, 644077 Omsk, Russia.
³ Institut de Química Computacional and Departament de Química, Universitat de Girona, C/Maria Aurèlia Capmany 69, Girona, Catalonia 17003, Spain.
⁴ Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences (UB RAS), 22 Sofia Kovalevskaya Street, Yekaterinburg,620990, Russian Federation.

PMID: 32643932
DOI: 10.1021/acs.joc.0c01299

Abstract

In this work, we describe the development of the rearrangement for 7-aryl-substituted oxazolo[5,4-b]pyridines treated with aluminum chloride into synthetically hard-to-reach benzo[c][1,7]naphthyridinones. The discovered rearrangement is applied to a variety of electron-rich (hetero)arene substrates. It offers the advantages of mild conditions (90 °C temperature), fast reaction rates (<4 h), compatibility with air moisture, and the use of inexpensive commercial reagents. The proposed reaction mechanism and key elementary reaction acts were studied in detail using quantum chemical calculations. The photophysical properties of the synthesized compounds were studied by steady-state UV-vis spectroscopy.