We developed a Jocic-type protocol for the construction of the pyrrolonaphthoxazepine (PNOX) core. After an initial investigation based on the isolation of a trichloromethyl carbinol derivative, we shifted our attention towards a multicomponent single-step protocol. Screening of a variety of bases and solvents led to the identification of the optimum conditions for the preparation of the key α-aryloxy carboxylic acids to undergo intramolecular cyclization. The novel chemical route significantly improved overall yields for the preparation of PNOX-based compounds and was successfully extended to the preparation of 1,4-benzoxazinone-based templates.

Federico, S., Khan, T., Relitti, N., Chemi, G., Brindisi, M., Brogi, S., et al. (2018). A Jocic-type approach for a practical and scalable synthesis of pyrrolonaphthoxazepine (PNOX)-based potent proapoptotic agents. TETRAHEDRON LETTERS, 59(51), 4466-4470 [10.1016/j.tetlet.2018.11.005].

A Jocic-type approach for a practical and scalable synthesis of pyrrolonaphthoxazepine (PNOX)-based potent proapoptotic agents

Federico, Stefano;Khan, Tuhina;Relitti, Nicola;Chemi, Giulia;Brindisi, Margherita;Brogi, Simone;Campiani, Giuseppe;Gemma, Sandra;Butini, Stefania
2018-01-01

Abstract

We developed a Jocic-type protocol for the construction of the pyrrolonaphthoxazepine (PNOX) core. After an initial investigation based on the isolation of a trichloromethyl carbinol derivative, we shifted our attention towards a multicomponent single-step protocol. Screening of a variety of bases and solvents led to the identification of the optimum conditions for the preparation of the key α-aryloxy carboxylic acids to undergo intramolecular cyclization. The novel chemical route significantly improved overall yields for the preparation of PNOX-based compounds and was successfully extended to the preparation of 1,4-benzoxazinone-based templates.
Federico, S., Khan, T., Relitti, N., Chemi, G., Brindisi, M., Brogi, S., et al. (2018). A Jocic-type approach for a practical and scalable synthesis of pyrrolonaphthoxazepine (PNOX)-based potent proapoptotic agents. TETRAHEDRON LETTERS, 59(51), 4466-4470 [10.1016/j.tetlet.2018.11.005].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/1063603