Three‐Component Reaction to 1,4,2‐Diazaborole‐Type Heteroarene Systems

Autor:	Gerhard Erker, Jun Li, Gerald Kehr, Constantin G. Daniliuc
Rok vydání:	2021
Předmět:	Heptane General Chemistry General Medicine Borane Medicinal chemistry Catalysis Cycloaddition Acylation chemistry.chemical_compound chemistry Nucleophile Reagent Product (mathematics) Pyrrole
Zdroj:	Angewandte Chemie. 133:27259-27267
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.202111946
Popis:	The borane FmesBH2 reacts in a three-component reaction with an isonitrile and a small series of organonitriles to give rare examples of the class of dihydro-1,4,2-diazaborole derivatives. In a related way, annulated BN-indolizine derivatives became conveniently available, as were dihydro-1,4,2-oxaza- or thiazaborole derivatives. The nucleophilic framework of a dihydro-1,4,2-diazaborole example allowed for an uncatalyzed acylation reaction. It also served as a 1,3-dipolar reagent and underwent a [3+2] cycloaddition/[4+2] cycloreversion sequence when treated with methyl propiolate to give the respective pyrrole product. The [3+2] cycloaddition product of a dihydro-1,4,2-diazaborole derivative with N-phenylmaleimide was isolated and its heterobicyclo[2.2.1]heptane derived structure characterized by X-ray diffraction.
Databáze:	OpenAIRE
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