New tetrahedral boron heterobicycles: Cyclocondensation of phenylboronic acid with β-keto butanoic acid N-acyl hydrazones

Antigoni Kotali; Anna Maniadaki; Elvira Kotali; Philip A. Harris; Ewa Różycka-Sokołowska; Piotr Bałczewski; John A. Joule

doi:10.1016/j.tetlet.2016.12.060

New tetrahedral boron heterobicycles: Cyclocondensation of phenylboronic acid with β-keto butanoic acid N-acyl hydrazones

Antigoni Kotali, Anna Maniadaki, Elvira Kotali, Philip A. Harris, Ewa Różycka-Sokołowska, Piotr Bałczewski, John A. Joule

Research output: Contribution to journal › Article › peer-review

Abstract

A series of 4-phenyl-2-aryl-8-methyl-6-oxo-7-phenylhydrazo-2H,4H,6H,7H,8H[1,3,4,2]-oxadiazaborolo[2,3-b][1,3,2]oxazaborines were prepared in high yields via the reaction of phenylboronic acid with various N-acylhydrazones of 3-keto-2-(2′-phenylhydrazono) butanoic acid in the presence of 4 Å molecular sieves. These derivatives represent a novel class of zwitterionic, tetrahedral boron heterocycles. Single crystal X-ray analysis of a representative boron containing product is reported.

Original language	English
Pages (from-to)	512-515
Number of pages	4
Journal	Tetrahedron Letters
Volume	58
Issue number	6
Early online date	23 Dec 2016
DOIs	https://doi.org/10.1016/j.tetlet.2016.12.060
Publication status	Published - 8 Feb 2017

Keywords

3-Keto-butanoic acid
Boron heterocycles
Cyclocondensation
Oxadiazaboroles
Oxazaborines
Phenylboronic acid

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10.1016/j.tetlet.2016.12.060

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title = "New tetrahedral boron heterobicycles: Cyclocondensation of phenylboronic acid with β-keto butanoic acid N-acyl hydrazones",

abstract = "A series of 4-phenyl-2-aryl-8-methyl-6-oxo-7-phenylhydrazo-2H,4H,6H,7H,8H[1,3,4,2]-oxadiazaborolo[2,3-b][1,3,2]oxazaborines were prepared in high yields via the reaction of phenylboronic acid with various N-acylhydrazones of 3-keto-2-(2′-phenylhydrazono) butanoic acid in the presence of 4 {\AA} molecular sieves. These derivatives represent a novel class of zwitterionic, tetrahedral boron heterocycles. Single crystal X-ray analysis of a representative boron containing product is reported.",

keywords = "3-Keto-butanoic acid, Boron heterocycles, Cyclocondensation, Oxadiazaboroles, Oxazaborines, Phenylboronic acid",

author = "Antigoni Kotali and Anna Maniadaki and Elvira Kotali and Harris, {Philip A.} and Ewa R{\'o}{\.z}ycka-Soko{\l}owska and Piotr Ba{\l}czewski and Joule, {John A.}",

year = "2017",

month = feb,

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doi = "10.1016/j.tetlet.2016.12.060",

language = "English",

volume = "58",

pages = "512--515",

journal = "Tetrahedron Letters",

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T1 - New tetrahedral boron heterobicycles

T2 - Cyclocondensation of phenylboronic acid with β-keto butanoic acid N-acyl hydrazones

AU - Kotali, Antigoni

AU - Maniadaki, Anna

AU - Kotali, Elvira

AU - Harris, Philip A.

AU - Różycka-Sokołowska, Ewa

AU - Bałczewski, Piotr

AU - Joule, John A.

PY - 2017/2/8

Y1 - 2017/2/8

N2 - A series of 4-phenyl-2-aryl-8-methyl-6-oxo-7-phenylhydrazo-2H,4H,6H,7H,8H[1,3,4,2]-oxadiazaborolo[2,3-b][1,3,2]oxazaborines were prepared in high yields via the reaction of phenylboronic acid with various N-acylhydrazones of 3-keto-2-(2′-phenylhydrazono) butanoic acid in the presence of 4 Å molecular sieves. These derivatives represent a novel class of zwitterionic, tetrahedral boron heterocycles. Single crystal X-ray analysis of a representative boron containing product is reported.

AB - A series of 4-phenyl-2-aryl-8-methyl-6-oxo-7-phenylhydrazo-2H,4H,6H,7H,8H[1,3,4,2]-oxadiazaborolo[2,3-b][1,3,2]oxazaborines were prepared in high yields via the reaction of phenylboronic acid with various N-acylhydrazones of 3-keto-2-(2′-phenylhydrazono) butanoic acid in the presence of 4 Å molecular sieves. These derivatives represent a novel class of zwitterionic, tetrahedral boron heterocycles. Single crystal X-ray analysis of a representative boron containing product is reported.

KW - 3-Keto-butanoic acid

KW - Boron heterocycles

KW - Cyclocondensation

KW - Oxadiazaboroles

KW - Oxazaborines

KW - Phenylboronic acid

UR - http://www.scopus.com/inward/record.url?scp=85008502034&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2016.12.060

DO - 10.1016/j.tetlet.2016.12.060

M3 - Article

AN - SCOPUS:85008502034

SN - 0040-4039

VL - 58

SP - 512

EP - 515

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

New tetrahedral boron heterobicycles: Cyclocondensation of phenylboronic acid with β-keto butanoic acid N-acyl hydrazones

Abstract

Keywords

Access to Document

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CCDC 1482807: Experimental Crystal Structure Determination

Cite this

New tetrahedral boron heterobicycles: Cyclocondensation of phenylboronic acid with β-keto butanoic acid N-acyl hydrazones

Abstract

Keywords

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Other files and links

Fingerprint

Datasets

CCDC 1482807: Experimental Crystal Structure Determination

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