The phosphinoboration of thiosemicarbazones

Author:

Baird Samuel R.1,Vogels Christopher M.1ORCID,Geier Stephen J.1ORCID,Watanabe Lara K.2ORCID,Binder Justin F.2ORCID,Macdonald Charles L. B.3ORCID,Westcott Stephen A.1ORCID

Affiliation:

1. Department of Chemistry and Biochemistry, Mount Allison University, Sackville, NB E4L 1G8, Canada

2. Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON N9B 3P4, Canada

3. Faculty of Science, Dalhousie University, Halifax, NS B3H 4R2, Canada

Abstract

This study reports on the exploration of the phosphinoboration reaction with several thiosemicarbazones (R5R4NC(S)NR3N=CR1R2). Reactions between either Ph2PBpin (pin = 1,2-O2C2Me4) or Ph2PBcat (cat = 1,2-O2C6H4) with thiosemicarbazones containing a terminal primary or secondary amine afforded boron-containing heterocyclic 1,3,4-thiadiazoline products in excellent yield. The addition of Ph2PBpin to thiosemicarbazones containing an NMe2 group in the terminal position generated novel five-membered heterocycles in moderate yield, which included boron, sulfur, and nitrogen atoms. Heterocyclization of the thiosemicarbazones occurs preferentially in the presence of functional groups such as acetyl and pyridyl groups.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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