α-Functionalized ketene N,S-acetals as two-carbon synthons in the reaction with 1,2-naphthoquinone 1-methide. Synthesis of 3-amino-1H-benzo[f]chromenes

Autor:	Dmitry V. Osipov, Anton V. Lukashenko, Vitaly А. Osyanin, Yuri N. Klimochkin
Rok vydání:	2020
Předmět:	chemistry.chemical_compound chemistry Organic Chemistry Synthon chemistry.chemical_element Ketene 1 2-Naphthoquinone Carbon Medicinal chemistry Cycloaddition
Zdroj:	Chemistry of Heterocyclic Compounds. 56:521-528
ISSN:	1573-8353 0009-3122
DOI:	10.1007/s10593-020-02694-5
Popis:	A series of 3-amino-1H-benzo[f]chromenes were obtained in the reaction of 1-[(dimethylamino)methyl]naphthalen-2-ol with push-pull ketene N,S-acetals containing an electron-withdrawing group in the α-position. It is assumed that the reaction proceeds as a [4+2] cycloaddition of ketene N,S-acetals to in situ generated 1,2-naphthoquinone 1-methide. Quantum-chemical methods were used to study the synchronicity of the Diels–Alder reaction.
Databáze:	OpenAIRE
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