Unprecedented cyclisations of calix[4]arenes under the Mitsunobu protocol.: Part 3:: Thiacalix[4] crowns versus dimers

被引：27

作者：

Csokai, V

Balázs, B

Tóth, G

Horváth, G

Bitter, I ^{[1
]}

机构：

[1] Budapest Univ Technol & Econ, Dept Organ Chem Technol, H-1521 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Inst Gen & Analyt Chem, Hungarian Acad Sci, Tech Analyt Res Grp, H-1111 Budapest, Hungary

[3] IVAX Drug Res Inst Ltd, H-1325 Budapest, Hungary

来源：

TETRAHEDRON | 2004年 / 60卷 / 52期

基金：

匈牙利科学研究基金会;

关键词：

thiacalix[4]arenes; cyclisations; thiacalix[4]crowns; dimers; Mitsunobu reaction;

D O I：

10.1016/j.tet.2004.10.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intermolecular couplings versus intramolecular ring closures were observed in the reaction of p-tert-butylthiacalix[4]arene and diethylene glycols affording dimers 2 and/or the inherently chiral 1,2-thiacalix[4]crown-3 derivatives 5 under the Mitsunobu protocol. The enantiomeric separation of 5a was achieved by chiral HPLC. The reaction of thiacalix[4]monocrowns 1 with diethylene glycols failed to give crowned thiacalix-tubes 7, instead biscrowns 8 were formed. Partially alkylated double thiacalix[4]arenes 10, 11 were obtained via the base promoted alkylations of a thiacalixarene dimer 2a containing diethyleneoxy linkers. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：12059 / 12066

页数：8

共 7 条

[1] Unprecedented cyclizations of calix[4]arenes with glycols under the Mitsunobu protocol. Part 4. An expedient route to thiacalix[4](aza and thia)crowns
Csokai, V
Bitter, I
SUPRAMOLECULAR CHEMISTRY, 2004, 16 (08) : 611 - 619
[2] Unprecedented cyclisations of calix[4]arenes with glycols under the Mitsunobu protocol.: Part 1:: A new perspective for the synthesis of calixcrowns
Csokai, V
Grün, A
Bitter, I
TETRAHEDRON LETTERS, 2003, 44 (25) : 4681 - 4684
[3] Unprecedented cyclizations of calix[4]arenes with glycols under the Mitsunobu protocol, Part 2.: O,O- and O,S-bridged calixarenes
Csokai, V
Grun, A
Balázs, B
Tóth, G
Horváth, G
Bitter, I
ORGANIC LETTERS, 2004, 6 (04) : 477 - 480
[4] Lower rim substituted tert-butylcalix[4]arenes -: (Part VI).: Synthesis and ionophoric properties of 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(3-diethoxyphosphorylpropoxy)calix[4]arene
Bochenska, M
Hoffmann, M
Lesinska, U
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2004, 49 (1-2) : 57 - 60
[5] Lower Rim Substituted tert-Butylcalix[4]arenes (Part VI). Synthesis and Ionophoric Properties of 5,11,17,23-Tetra-tert-Butyl-25,26,27,28-Tetrakis(3-Diethoxyphosphorylpropoxy)Calix[4]arene
M. Bocheńska
M. Hoffmann
U. Lesińska
Journal of inclusion phenomena and macrocyclic chemistry, 2004, 49 : 57 - 60
[6] Reverse shoulder arthroplasty versus hemiarthroplasty versus non-surgical treatment for older adults with acute 3-or 4-part fractures of the proximal humerus: study protocol for a randomised controlled trial (PROFHER-2: PROximal Fracture of Humerus Evaluation by Randomisation - Trial Number 2)
Rangan, Amar
Gwilym, Stephen
Keding, Ada
Corbacho, Belen
Kottam, Lucksy
Arundel, Catherine
Coleman, Elizabeth
DiMascio, Livio
Hewitt, Catherine
Jones, Valerie
Kassam, Jamila
McDaid, Catriona
Mitchell, Natasha
Mott, Andrew
O'Carroll, Grace
Tharmanathan, Puvan
Torgerson, David
TRIALS, 2023, 24 (01)
[7] Reverse shoulder arthroplasty versus hemiarthroplasty versus non-surgical treatment for older adults with acute 3- or 4-part fractures of the proximal humerus: study protocol for a randomised controlled trial (PROFHER-2: PROximal Fracture of Humerus Evaluation by Randomisation – Trial Number 2)
Amar Rangan
Stephen Gwilym
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