Molecular Iodine-Promoted [3+2] Oxidative Cyclization for the Synthesis of Heteroarene-Fused [1,2,4] Thiadiazoles/Selenadiazoles

被引：8

作者：

Chen, Jin-Yu ^{[1
]}

Selvaraju, Manikandan ^{[2
]}

Lin, Yen-Tzu ^{[1
]}

Dhole, Sandip ^{[1
]}

Lin, Chih-Yu ^{[1
]}

Sun, Chung-Ming ^{[1
,3
]}

机构：

[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30010, Taiwan

[2] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

[3] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 80708, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 08期

关键词：

N BOND FORMATION; 1,2,4-TRIAZOLES; ACCESS; 1,2,4-SELENADIAZOLES;

D O I：

10.1021/acs.joc.0c00421

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new classes of heteroarene-fused [1,2,4]thiadiazole and [1,2,4]selenadiazole are synthesized through the iodine-mediated [3 + 2] oxidative cyclization of 2-aminoheteroarenes and isothiocyanates/isoselenocyanates. This oxidative [3 + 2] annulation strategy is highly regiospecific to proceed a selective C-N bond formation at the endo-nitrogen of 2-aminoheteroarenes followed by an intramolecular oxidative N-S/N-Se bond formation. It is the first example of an I-2-mediated oxidative nitrogen-selenium (N-Se) bond formation.

引用

页码：5570 / 5579

页数：10

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