One-pot synthesis of 2-imino-1,3,4-thiadiazolines from acylhydrazides and isothiocyanates
Su Been Kim
Department of Chemistry, Research Institute of Basic Sciences, Incheon National University, Incheon, South Korea
Search for more papers by this authorSang Eun Baek
Department of Chemistry, Research Institute of Basic Sciences, Incheon National University, Incheon, South Korea
Search for more papers by this authorJae Hyeok Lim
Department of Chemistry, Research Institute of Basic Sciences, Incheon National University, Incheon, South Korea
Search for more papers by this authorCorresponding Author
Jinho Kim
Department of Chemistry, Research Institute of Basic Sciences, Incheon National University, Incheon, South Korea
Correspondence
Jinho Kim, Department of Chemistry, Research Institute of Basic Sciences, Incheon National University, 119 Academy-ro, Yeonsu-gu, Incheon 22012, South Korea.
Email: [email protected]
Search for more papers by this authorSu Been Kim
Department of Chemistry, Research Institute of Basic Sciences, Incheon National University, Incheon, South Korea
Search for more papers by this authorSang Eun Baek
Department of Chemistry, Research Institute of Basic Sciences, Incheon National University, Incheon, South Korea
Search for more papers by this authorJae Hyeok Lim
Department of Chemistry, Research Institute of Basic Sciences, Incheon National University, Incheon, South Korea
Search for more papers by this authorCorresponding Author
Jinho Kim
Department of Chemistry, Research Institute of Basic Sciences, Incheon National University, Incheon, South Korea
Correspondence
Jinho Kim, Department of Chemistry, Research Institute of Basic Sciences, Incheon National University, 119 Academy-ro, Yeonsu-gu, Incheon 22012, South Korea.
Email: [email protected]
Search for more papers by this authorSu Been Kim and Sang Eun Baek contributed equally to this study.
Dedicated to Professor Sukbok Chang on the occasion of his 60th birthday
Funding information: Incheon National University Research Grant
Abstract
A one-pot synthesis of 2-imino-1,3,4-thiadiazolines was successfully achieved under mild conditions. The developed synthesis involves Fe(Pc)-catalyzed aerobic oxidation of acylhydrazides followed by P(NMe2)3-mediated annulation of the in situ generated N-acyldiazene with isothiocyanates. The present annulation showed broad substrate scope with good functional group tolerance, and was effective on gram scale.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
Supporting Information
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