The phosphinoboration of thiosemicarbazones
| Autor: | Samuel R. Baird, Christopher M. Vogels, Stephen J. Geier, Lara K. Watanabe, Justin F. Binder, Charles L. B. Macdonald, Stephen A. Westcott |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Canadian Journal of Chemistry. |
| ISSN: | 1480-3291 0008-4042 |
| DOI: | 10.1139/cjc-2022-0088 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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