Microwave irradiation of various dialdehydes and chiral diamines afforded chiral macrocyclic imines in moderate to good yields. Linked dialdehydes predominantly form [2+2] macrocycles whereas dialdehydes without linkers yield [3+3] macrocycles. This is the first report of template-free synthesis of calixsalen-type macrocycles formed in shorter reaction times under microwave conditions. In all the reactions, the salts of chiral diamines were used in contrast to the free diamines normally employed. © 2005 Elsevier Ltd. All rights reserved.

Balasubramanian Viswanathan

Thirukkallam Kanthadai Varadarajan

Babu Varghese

aldehyde

calixarene

CALIXSALEN

macrocyclic compound

unclassified drug

article

chirality

matrix assisted laser desorption ionization time of flight mass spectrometry

Microwave irradiation

nuclear magnetic resonance

Polymerization

reaction time

synthesis

X ray crystallography

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Tetrahedron Letters

A facile method for the synthesis of (2R,3R)-1,4-dimethoxy-1,1,4,4- tetrasubstituted-2,3-butanediols involving oxidative cleavage of benzylidene acetal as a key step is described. These sterically hindered diols unusually formed cyclic sulfites as the major product under methanesulfonylation reaction conditions. Copyright © Taylor & Francis Group, LLC.

Synthetic Communications

Facile synthesis and unusual methanesulfonylation reaction of (2R,3R)-1,4-dimethoxy-1,1,4,4-tetrasubstituted-2,3-butanediols

The synthesis and crystal structure of macrocyclic Schiff bases formed in a short reaction time from (1R,2R)-diammoniumcyclohexane mono-(+)-tartrate were investigated. Microwave irradiation of a mixture of bis-(hydroxyaldehydes) and chiral diamines in the presence of potassium carbonate afforded chiral macrocyclic tetraimines in moderate good yields. The structure of the [2+2] macrocycle was confirmed by both MALDI-TOF analysis and single-crystal XRD. The X-ray crystallographic analysis of the unsolved macrocycle Schiff base grown from a hexane-ethyl acetate solution confirmed the cyclic nature of the structure. The macrocycle stack in an eclipsed manner along the crystallographic a-axis, giving rise to infinite columns with macropores. The results show that the crystal structure of the macrocycles resembles that of calixarene and exhibits columnar staking in the solid state.

Organic and Biomolecular Chemistry

Synthesis and crystal structure of [2 + 2] calixsalens

Recueil des Travaux Chimiques des Pays-Bas

Synthesis of new macrocyclic ligands for hetero-multinuclear transition-metal complexes

Who's Who

Kennard, Dr Olga, (Lady Burgen), (born 23 March 1924), Director, Cambridge Crystallographic Data Centre, 1965–97

Organic & Biomolecular Chemistry

The synthesis of trianglimines: on the scope and limitations of the [3 + 3] cyclocondensation reaction between (1R,2R)-diaminocyclohexane and aromatic dicarboxaldehydes

Syntheses of large-membered macrocycles having multiple hydrogen bonding moieties

Tetrahedron: Asymmetry

Synthesis of novel enantiomerically pure trianglimine and trianglamine macrocycles

Microwave assisted cyclocondensation of dialdehydes with chiral diamines forming calixsalen type macrocycles

Journal	Data powered by TypesetTetrahedron Letters
Publisher	Data powered by TypesetElsevier Ltd
ISSN	00404039
Open Access	No