I2-Mediated Oxidative C-N and N-S Bond Formation in Water: A Metal-Free Synthesis of 4,5-Disubstituted/N-Fused 3-Amino-1,2,4-triazoles and 3-Substituted 5-Amino-1,2,4-thiadiazoles

被引：46

作者：

Jatangi, Nagesh ^{[1
]}

Tumula, Nagaraju ^{[1
]}

Palakodety, Radha Krishna ^{[1
]}

Nakka, Mangarao ^{[1
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 10期

关键词：

ONE-POT SYNTHESIS; MOLECULAR-IODINE; ANTIFUNGAL AGENTS; 1,2,4-TRIAZOLES; DERIVATIVES; 1,2,4-THIADIAZOLES; DIMERIZATION; EFFICIENT;

D O I：

10.1021/acs.joc.8b00753

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An environmentally benign and convenient strategy for the synthesis of 4,5-disubstituted/N-fused 3-amino-1,2,4-triazoles and 3-substituted 5-amino-1,2,4-thiadiazoles from isothiocyanates has been developed. This metal-free method involves I-2-mediated oxidative C-N and N-S bond formations in water. Furthermore, this facile protocol exhibited excellent substrate tolerance in good to high yields and scalable fashion.

引用

页码：5715 / 5723

页数：9

共 43 条

[1] Electrochemical Oxidative Intramolecular N-S Bond Formation: Synthesis of 3-Substituted 5-Amino-1,2,4-Thiadiazoles
Yang, Zan
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Hu, Liping
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JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05) : 3358 - 3363
[2] Synthesis of 5-Amino and 3,5-Diamino Substituted 1,2,4-Thiadiazoles by I2-Mediated Oxidative N-S Bond Formation
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Zhou, Yiming
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[3] I2-Catalyzed Oxidative N-S Bond Formation: Metal-Free Regiospecific Synthesis of N-Fused and 3,4-Disubstituted 5-Imino-1,2,4-thiadiazoles
Tumula, Nagaraju
Jatangi, Nagesh
Palakodety, Radha Krishna
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Nakka, Mangarao
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (10) : 5310 - 5316
[4] Hypervalent Iodine(III) Mediated Synthesis of 3-Substituted 5-Amino-1,2,4-thiadiazoles through Intramolecular Oxidative S-N Bond Formation
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[5] Copper-catalyzed synthesis of 3-substituted-5-amino-1,2,4-thiadiazoles via intramolecular N-S bond formation
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[6] One-Pot Synthesis of 3-Aryl-5-amino-1,2,4-thiadiazoles from Imidates and Thioureas by I2-Mediated Oxidative Construction of the N-S Bond
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Lai, Zhenzhen
Xia, Qiangqiang
Yuan, Jiangpei
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[7] Copper-Catalyzed Aerobic Oxidative [3+2] Annulation for the Synthesis of 5-Amino/Imino-Substituted 1,2,4-Thiadiazoles through C-N/N-S Bond Formation
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[8] Transition-metal-free S-N bond formation: synthesis of 5-amino-1,2,4-thiadiazoles from isothiocyanates and amidines
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[9] Synthesis of fused 3-amino-1,2,4-triazoles via sequential addition of aryl hydrazines to isothiocyanates and I2-mediated cyclodesulfurization
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TETRAHEDRON, 2018, 74 (24) : 3069 - 3073
[10] Rapid, microwave-assisted synthesis of N1-substituted 3-amino-1,2,4-triazoles
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TETRAHEDRON LETTERS, 2009, 50 (15) : 1667 - 1670

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