Inter and intramolecular copper(I)-catalyzed 1,3-dipolar cycloaddition of azido-alkynes: synthesis of furanotriazole macrocycles

Tetrahedron Letters

Volumn 48, Issue 33, 2007, Pages 5869-5872

  Chandrasekhar, Srivari ^a   Rao, Chennamaneni Lohitha ^a   Nagesh, Chidalla ^a   Reddy, Chada Raji ^a   Sridhar, Balasubramanian ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

'Click' reaction; 1,3 Dipolar cycloaddition; Macrocycles

Indexed keywords

ALKYNE; AZIDE; COPPER; FURANOTRIAZOLE; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLOADDITION; ESTERIFICATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR DYNAMICS; OLIGOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 34447539753     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.062     Document Type: Article

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30. Molecular dynamics for the energy minimized conformation of 2 were carried out using Insight II program on a Silicon Graphics work station.
31. We have tried to prepare the cyclic monomer from compound 1 under high dilution conditions to compare the spectral data with cyclic dimer 2, however, formation of the cyclic monomer was not observed.
32. 18 {A figure is presented}
33. -1, F(0 0 0) = 536, λ = 0.71073 Å. Data collection yielded 11224 reflections resulting in 1206 unique, averaged reflections, 1196 with I > 2σ(I). Full-matrix least-squares refinement led to a final R = 0.0261, wR = 0.0712 and GOF = 1.128. Intensity data were measured on a Bruker Smart Apex with CCD area detector. Crystallographic data has been deposited for compound 4 with the Cambridge Crystallographic Data Centre, [CCDC No. 649353]. Copies of the data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html or CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223 336 033; e-mail: deposit@ccdc.cam.ac.uk).
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