Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles

The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utili...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-06, Vol.79 (12), p.5752-5762
Main Authors: Mishra, Kunj B, Tiwari, Vinod K
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Azides - chemistry
Click Chemistry
Crystallography, X-Ray
Cyclization
Epichlorohydrin - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Morpholines - chemical synthesis
Morpholines - chemistry
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utilized for the synthesis of a diverse range of morpholine-fused triazoles of chemotherapeutic value. The structure of all developed compounds has been elucidated using IR, NMR, MS, and elemental analysis, where four of them have been characterized by single-crystal X-ray analysis.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo500890w