Intramolecular Azo Coupling Reaction of Binaphthyl Compounds: Synthesis of Pyrazole-Containing Helicene-Like Molecules

被引：1

作者：

Yoshida, Yasushi ^{[1
]}

Aso, Naoyuki ^{[1
]}

Karatsu, Takashi ^{[1
]}

Mino, Takashi ^{[1
]}

Sakamoto, Masami ^{[1
]}

机构：

[1] Chiba Univ, Mol Chiral Res Ctr, Grad Sch Engn, Chiba, Chiba 2638522, Japan

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 19期

关键词：

ONE HUNDRED YEARS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE SYNTHESES;

D O I：

10.1021/acs.orglett.3c00974

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for accessing pyrazole-containing helicene-like molecules from easily accessible NOBIN derivatives was developed. The reaction proceeded efficiently via diazonium salt intermediates, which provided a series of helicene-like molecular products in yields of 77%-89% regardless of their steric and electronic natures. The photophysical properties of the products were investigated. The 3,3 '-disubstituted molecules showed a characteristic blue shift in their emission spectra. Product derivatizations were conducted, and interesting reactivities toward nucleophiles were observed.

引用

页码：3412 / 3416

页数：5

共 35 条

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[33] Efficient Synthesis of Pyrido[3,4-c ]cinnolines and Pyrido[3,2-c ]cinnolines by Intramolecular Azo Coupling Reaction of 4,6-Diaryl-3-pyridine Diazonium Salts and Study of Their Antiviral Activity
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