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

被引：4

作者：

Kotali, Antigoni ^{[1
]}

Maniadaki, Anna ^{[1
]}

Kotali, Elvira ^{[1
]}

Harris, Philip A. ^{[2
]}

Rozycka-Sokolowska, Ewa ^{[3
]}

Balczewski, Piotr ^{[3
,4
]}

Joulee, John A. ^{[5
]}

机构：

[1] Univ Thessaloniki, Dept Chem Engn, Organ Chem Lab, Thessaloniki 54124, Greece

[2] GlaxoSmithKline, 1250 South Collegeville Rd,POB 5089, Collegeville, PA 19426 USA

[3] Jan Dlugosz Univ Czestochowa, Inst Chem Environm Protect & Biotechnol, PL-42201 Czestochowa, Poland

[4] Polish Acad Sci, Dept Heteroorgan Chem, Ctr Mol & Macromol Studies, PL-90363 Lodz, Poland

[5] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 23期

关键词：

hydrazones; cyclocondensation; boron heterocycles; boron triacetate; 1,3,4,2]oxadiazaboroles; 1,3,2]oxazaborines; BETA-KETOACIDS; EFFICIENT CONSTRUCTION; DERIVATIVES; MECHANISM; DISCOVERY; NITROGEN;

D O I：

10.1055/s-0035-1562610

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. Xray single-crystal analyses of one of the starting (acylhydrazono) butanoic acids as well as of one heterocyclic boron product are reported.

引用

页码：4117 / 4125

页数：9

共 38 条

[1] Potent and selective inhibitors of the proteasome: Dipeptidyl boronic acids
Adams, J
Behnke, M
Chen, SW
Cruickshank, AA
Dick, LR
Grenier, L
Klunder, JM
Ma, YT
Plamondon, L
Stein, RL
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (04) : 333 - 338
[2] Anti-breast cancer activity of some novel 1,2-dihydropyridine, thiophene and thiazole derivatives
Al-Said, Mansour S.
Bashandy, Mahmoud S.
Al-Qasoumi, Saleh I.
Ghorab, Mostafa M.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) : 137 - 141
[3] Directed ortho metalation-boronation and Suzuki-Miyaura cross coupling of pyridine derivatives:: A one-pot protocol to substituted azabiaryls
Alessi, Manlio
Larkin, Andrew L.
Ogilvie, Kevin A.
Green, Laine A.
Lai, Sunny
Lopez, Simon
Snieckus, Victor
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (05) : 1588 - 1594
[4] ALI H.A., 2005, CONT ASPECTS BORON C
[5] Synthesis and biological evaluation of some hydrazone derivatives as new anticandidal and anticancer agents
Altintop, Mehlika Dilek
Ozdemir, Ahmet
Turan-Zitouni, Gulhan
Ilgin, Sinem
Atli, Ozlem
Iscan, Gokalp
Kaplancikli, Zafer Asim
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 58 : 299 - 307
[6] [Anonymous], 2009, ARKIVOC, P81
[7] Discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (AN2690), for the potential treatment of onychomycosis
Baker, Stephen J.
Zhang, Yong-Kang
Akama, Tsutomu
Lau, Agnes
Zhou, Huchen
Hernandez, Vincent
Mao, Weimin
Alley, M. R. K.
Sanders, Virginia
Plattner, Jacob J.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (15) : 4447 - 4450
[8] PATTERNS IN HYDROGEN BONDING - FUNCTIONALITY AND GRAPH SET ANALYSIS IN CRYSTALS
BERNSTEIN, J
DAVIS, RE
SHIMONI, L
CHANG, NL
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (15) : 1555 - 1573
[9] Copying nature's mechanism for the decarboxylation of beta-keto acids into catalytic antibodies by reactive immunization
Bjornestedt, R
Zhong, GF
Lerner, RA
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (47) : 11720 - 11724
[10] Synthesis of β-ketoesters from renewable resources and Meldrum's acid
Brinkerhoff, Rafael C.
Tarazona, Hernan F.
de Oliveira, Patrick M.
Flores, Darlene C.
Montes D'Oca, Caroline Da R.
Russowsky, Dennis
Montes D'Oca, Marcelo G.
[J]. RSC ADVANCES, 2014, 4 (91): : 49556 - 49559

← 1 2 3 4 →