Nitro-Spirocyclization of Biaryl Ynones with tert-Butyl Nitrite: Access to NO2-Substituted Spiro[5,5]trienones

被引：17

作者：

Li, Yang ^{[1
]}

Li, Lijun ^{[1
]}

Guo, Changyou ^{[1
]}

Yan, Qinqin ^{[1
]}

Zhou, Hongxun ^{[1
]}

Wang, Ying ^{[1
]}

Liu, Zhong-Quan ^{[2
]}

Li, Zejiang ^{[1
]}

机构：

[1] Hebei Univ, Coll Chem & Mat Sci, Key Lab Med Chem & Mol Diag, Key Lab Chem Biol Hebei Prov,Minist Educ, Baoding 071002, Hebei, Peoples R China

[2] Nanjing Univ Chinese Med, Coll Pharm, Jiangsu Collaborat Innovat Ctr Chinese Med Resourc, Nanjing 210023, Jiangsu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 07期

基金：

中国国家自然科学基金;

关键词：

STEREOSELECTIVE NITRATION; MEDIATED DEAROMATIZATION; N-ARYLPROPIOLAMIDES; AROMATIC-COMPOUNDS; CHARGE-TRANSFER; ALKYNES; CYCLIZATION; OLEFINS; (BUONO)-BU-T; CARBOCYCLIZATION;

D O I：

10.1021/acs.joc.3c00087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal/peroxide-free involved simple cascade 6exo-trig spirocyclization of tert-butyl nitrite with biaryl ynones has been finished, which resulted in various NO2-modified spiro[5,5]trienones with good regioselectivity/yields. A variety of scaled-up experiments, reduction/epoxidation operations, and mechanistic studies were performed to verify the merits and spirocyclization process of this radical system. Finally, the structure of the spirocycles was confirmed by single-crystal X-ray diffraction.

引用

页码：4854 / 4862

页数：9

共 31 条

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