Synthesis 2016; 48(23): 4117-4125
DOI: 10.1055/s-0035-1562610
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Bicyclic Boron Heterocycles Containing [1,3,4,2]Oxadiazaborole and [1,3,2]Oxazaborine

Antigoni Kotali*
a   Laboratory of Organic Chemistry, Department of Chemical Engineering, University of Thessaloniki, Thessaloniki 54124, Greece   Email: kotali@eng.auth.gr
,
Anna Maniadaki
a   Laboratory of Organic Chemistry, Department of Chemical Engineering, University of Thessaloniki, Thessaloniki 54124, Greece   Email: kotali@eng.auth.gr
,
Elvira Kotali
a   Laboratory of Organic Chemistry, Department of Chemical Engineering, University of Thessaloniki, Thessaloniki 54124, Greece   Email: kotali@eng.auth.gr
,
Philip A. Harris
b   GlaxoSmithKline, 1250 South Collegeville Road, P.O. Box 5089, Collegeville, PA 19426-0989, USA
,
Ewa Różycka-Sokołowska
c   Institute of Chemistry, Environmental Protection and Biotechnology, Jan Długosz University in Częstochowa, 42-201 Częstochowa, Poland
,
Piotr Bałczewski
c   Institute of Chemistry, Environmental Protection and Biotechnology, Jan Długosz University in Częstochowa, 42-201 Częstochowa, Poland
d   Department of Heteroorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Łódz, Poland
,
John A. Joule
e   The School of Chemistry, The University of Manchester, Manchester M13 9PL, UK
› Author Affiliations
Further Information

Publication History

Received: 24 June 2016

Accepted after revision: 11 July 2016

Publication Date:
17 August 2016 (online)


Abstract

Boron triacetate, generated in situ, reacts with various 3-(2-acyl­hydrazono)-2-(2-phenylhydrazono)butanoic acids to give 4-acetoxy-2-aryl-8-methyl-6-oxo-7-phenylhydrazono-2H,4H,6H,7H,8H-[1,3,4,2]oxa­diazaborolo[2,3-b][1,3,2]oxazaborines in good yields. These derivatives represent a class of new zwitterionic, tetrahedral boron heterocycles. X-ray single-crystal analyses of one of the starting (acylhydrazono)butanoic acids as well as of one heterocyclic boron product are reported.

 
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