Transition metal-free [3 + 3] annulation of cyclopropanols with ß-enamine esters to assemble nicotinate derivatives.

Zhan, Jun-Long; Zhu, Lin; Bai, Jia-Nan; Liu, Jian-Bo; Zhang, Shi-Han; Xie, Yao-Qiang; Hu, Bo-Mei; Wang, Yang; Han, Wen-Jun

Zhan, Jun-Long; Zhu, Lin; Bai, Jia-Nan; Liu, Jian-Bo; Zhang, Shi-Han; Xie, Yao-Qiang; Hu, Bo-Mei; Wang, Yang; Han, Wen-Jun.

Afiliação

Zhan JL; Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs, College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China. zhanjl13@126.com.
Zhu L; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. China.
Bai JN; Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs, College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China. zhanjl13@126.com.
Liu JB; Henan Province Key Laboratory of New Opto-electronic Functional Materials, Anyang, 455000, P. R. China.
Zhang SH; Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs, College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China. zhanjl13@126.com.
Xie YQ; Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs, College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China. zhanjl13@126.com.
Hu BM; Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs, College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China. zhanjl13@126.com.
Wang Y; Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs, College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China. zhanjl13@126.com.
Han WJ; Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs, College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang, 455000, P. R. China. zhanjl13@126.com.

Org Biomol Chem ; 21(45): 8984-8988, 2023 Nov 22.

Article em En | MEDLINE | ID: mdl-37937487

ABSTRACT

ABSTRACT

A metal-free and efficient approach for the synthesis of structurally important nicotinates through 4-HO-TEMPO-mediated [3 + 3] annulation of cyclopropanols with ß-enamine esters is presented. This protocol features high atom efficiency, green waste, simple operation and broad substrate scope. Moreover, the experiments of gram-scale synthesis and recovery of oxidants make this strategy more sustainable and practical.

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Biomol Chem Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2023 Tipo de documento: Article

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