Chemoselective ring closure of thiacalix[4]arene-1,3-bis(N-ω- hydroxyalkylamides) via the Mitsunobu reaction

Viktor Csokai, A. Simon, B. Balázs, Gábor Tóth, I. Bitter

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Chemoselective intramolecular ring closure on the phenolic OH groups of p-tert-butylthiacalix[4]arene-1,3-bis(N-ω-hydroxyalkylamides) attained under Mitsunobu conditions affords inherently chiral macrocycles capped by carboxamide bridges. Oxazoline or oxazine cyclization products derived from self-condensation of the hydroxyalkylamide moieties were not isolated. In one case the detection of enantiomers was achieved by chiral HPLC.

Original languageEnglish
Pages (from-to)2850-2856
Number of pages7
JournalTetrahedron
Volume62
Issue number12
DOIs
Publication statusPublished - Mar 20 2006

Fingerprint

Oxazines
Enantiomers
Cyclization
Condensation
High Pressure Liquid Chromatography
p-tert-butylthiacalix(4)arene
thiacalix(4)arene

Keywords

  • Cyclizations
  • Hydroxyalkylamides
  • Mitsunobu reaction
  • Thiacalix[4]arenes

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Chemoselective ring closure of thiacalix[4]arene-1,3-bis(N-ω- hydroxyalkylamides) via the Mitsunobu reaction. / Csokai, Viktor; Simon, A.; Balázs, B.; Tóth, Gábor; Bitter, I.

In: Tetrahedron, Vol. 62, No. 12, 20.03.2006, p. 2850-2856.

Research output: Contribution to journalArticle

@article{3df06c6a301a4f0fa795eb80983c82d8,
title = "Chemoselective ring closure of thiacalix[4]arene-1,3-bis(N-ω- hydroxyalkylamides) via the Mitsunobu reaction",
abstract = "Chemoselective intramolecular ring closure on the phenolic OH groups of p-tert-butylthiacalix[4]arene-1,3-bis(N-ω-hydroxyalkylamides) attained under Mitsunobu conditions affords inherently chiral macrocycles capped by carboxamide bridges. Oxazoline or oxazine cyclization products derived from self-condensation of the hydroxyalkylamide moieties were not isolated. In one case the detection of enantiomers was achieved by chiral HPLC.",
keywords = "Cyclizations, Hydroxyalkylamides, Mitsunobu reaction, Thiacalix[4]arenes",
author = "Viktor Csokai and A. Simon and B. Bal{\'a}zs and G{\'a}bor T{\'o}th and I. Bitter",
year = "2006",
month = "3",
day = "20",
doi = "10.1016/j.tet.2006.01.017",
language = "English",
volume = "62",
pages = "2850--2856",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "12",

}

TY - JOUR

T1 - Chemoselective ring closure of thiacalix[4]arene-1,3-bis(N-ω- hydroxyalkylamides) via the Mitsunobu reaction

AU - Csokai, Viktor

AU - Simon, A.

AU - Balázs, B.

AU - Tóth, Gábor

AU - Bitter, I.

PY - 2006/3/20

Y1 - 2006/3/20

N2 - Chemoselective intramolecular ring closure on the phenolic OH groups of p-tert-butylthiacalix[4]arene-1,3-bis(N-ω-hydroxyalkylamides) attained under Mitsunobu conditions affords inherently chiral macrocycles capped by carboxamide bridges. Oxazoline or oxazine cyclization products derived from self-condensation of the hydroxyalkylamide moieties were not isolated. In one case the detection of enantiomers was achieved by chiral HPLC.

AB - Chemoselective intramolecular ring closure on the phenolic OH groups of p-tert-butylthiacalix[4]arene-1,3-bis(N-ω-hydroxyalkylamides) attained under Mitsunobu conditions affords inherently chiral macrocycles capped by carboxamide bridges. Oxazoline or oxazine cyclization products derived from self-condensation of the hydroxyalkylamide moieties were not isolated. In one case the detection of enantiomers was achieved by chiral HPLC.

KW - Cyclizations

KW - Hydroxyalkylamides

KW - Mitsunobu reaction

KW - Thiacalix[4]arenes

UR - http://www.scopus.com/inward/record.url?scp=32844468457&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=32844468457&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2006.01.017

DO - 10.1016/j.tet.2006.01.017

M3 - Article

AN - SCOPUS:32844468457

VL - 62

SP - 2850

EP - 2856

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 12

ER -