Synthesis 2016; 48(01): 122-130
DOI: 10.1055/s-0035-1560508
paper
© Georg Thieme Verlag Stuttgart · New York

Catalyst-Free Regioselective C-3 Nitrosation of Imidazopyridines with tert-Butyl Nitrite under Neutral Conditions

Daoshan Yang
Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China   Email: huawang_qfnu@126.com
,
Kelu Yan
Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China   Email: huawang_qfnu@126.com
,
Wei Wei
Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China   Email: huawang_qfnu@126.com
,
Yao Liu
Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China   Email: huawang_qfnu@126.com
,
Mengqi Zhang
Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China   Email: huawang_qfnu@126.com
,
Caixia Zhao
Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China   Email: huawang_qfnu@126.com
,
Laijin Tian
Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China   Email: huawang_qfnu@126.com
,
Hua Wang*
Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China   Email: huawang_qfnu@126.com
› Author Affiliations
Further Information

Publication History

Received: 05 August 2015

Accepted after revision: 25 September 2015

Publication Date:
30 October 2015 (online)


Abstract

We have successfully developed a novel and efficient catalyst-free method for the synthesis of 3-nitroso-substituted imidazopyridines, from readily available imidazo[1,2-a]pyridines and tert-butyl nitrite, in good to excellent yields. Importantly, the use of transition-metal catalysts, stoichiometric amounts of acids, and toxic or potentially dangerous oxidants is avoided. This easy and practical method complements nitrosation reactions by expanding the scope and practicality, and should attract much attention in synthetic and pharmaceutical chemistry.

Supporting Information

 
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