Synthesis of Naphthopyrans via Formal (3+3)-Annulation of Propargylic (Aza)-<i>para</i>-Quinone Methides with Naphthols.

Zhang, Xiang-Zhi; Li, Bao Qiong; Qiu, Zong-Wang; Ma, Ai-Jun; Peng, Jin-Bao; Du, Ji-Yuan; Feng, Na; Xu, Xue-Tao; Pan, Han-Peng

Synthesis of Naphthopyrans via Formal (3+3)-Annulation of Propargylic (Aza)-para-Quinone Methides with Naphthols.

Zhang, Xiang-Zhi; Li, Bao Qiong; Qiu, Zong-Wang; Ma, Ai-Jun; Peng, Jin-Bao; Du, Ji-Yuan; Feng, Na; Xu, Xue-Tao; Pan, Han-Peng.

Afiliação

Zhang XZ; School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, People's Republic of China.
Li BQ; School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, People's Republic of China.
Qiu ZW; School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, People's Republic of China.
Ma AJ; School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, People's Republic of China.
Peng JB; School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, People's Republic of China.
Du JY; College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong 252059, People's Republic of China.
Feng N; School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, People's Republic of China.
Xu XT; School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, People's Republic of China.
Pan HP; School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, People's Republic of China.

J Org Chem ; 85(20): 13306-13316, 2020 10 16.

Article em En | MEDLINE | ID: mdl-32991169

ABSTRACT

ABSTRACT

Herein, we report an efficient Brønsted acid-catalyzed formal (3+3)-annulation of (aza)-para-quinone methides generated in situ from propargylic alcohols with naphthol derivatives, which involves a 1,8-conjugate addition/6-endo annulation process. This protocol provides an effective method for preparing important functionalized pyranocoumarins under mild conditions.

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Texto completo: 1 Bases de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2020 Tipo de documento: Article