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Open AccessArticle

Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®)

1
Medicinal Chemistry Research Group, Research Centre for Natural Sciences, Magyar tudósok krt. 2, H-1117 Budapest, Hungary
2
Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., P. O. Box 100, H-1475 Budapest, Hungary
*
Authors to whom correspondence should be addressed.
Chemistry 2020, 2(2), 600-612; https://doi.org/10.3390/chemistry2020037
Received: 13 May 2020 / Revised: 3 June 2020 / Accepted: 9 June 2020 / Published: 16 June 2020
(This article belongs to the Special Issue Organic Chemistry Research in Hungary)
A sequential one-pot two-step protocol has been elaborated for the synthesis of naphthoxazinones from 2-naphthol, methyl carbamate, and aromatic aldehydes. First, a three-component reaction was optimized with the dehydrating additive propylphosphonic anhydride (T3P®), resulting in 1-carbamatoalkyl 2-naphthols in good to excellent yields. Following the successful multicomponent approach, intramolecular acylation was performed at high temperature, again with the contribution of T3P®, resulting in naphthoxazinone derivatives in moderate yields. These two steps were optimized together in one-pot as well, and the sequential rise in the requisite temperature eventuated the optimal procedure for the multistep cascade. View Full-Text
Keywords: multicomponent reaction; 1-carbamatoalkyl 2-naphthols; naphthoxazinones; T3P®; mechanism multicomponent reaction; 1-carbamatoalkyl 2-naphthols; naphthoxazinones; T3P®; mechanism
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MDPI and ACS Style

Varga, V.; Ábrányi-Balogh, P.; Milen, M. Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®). Chemistry 2020, 2, 600-612.

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