Intramolecular copper(I)-catalyzed 1,3-dipolar cycloaddition of azido-alkynes: Synthesis of triazolo-benzoxazepine derivatives and their biological evaluation

Tetrahedron Letters

Volumn 52, Issue 7, 2011, Pages 806-808

  Chandrasekhar, Srivari ^a   Seenaiah, Mallikanti ^a   Kumar, Abhishek ^a   Reddy, Chada Raji ^a   Mamidyala, Suman Kumar ^a   Kumar, Chityal Ganesh ^a   Balasubramanian, Sridhar ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,3 Dipolar cycloaddition; Anti microbial; Click chemistry; Copper catalysis; Triazolo benzoxazepine

Indexed keywords

1,2,3 TRIAZOLO[5,1 C] [1,4] BENZOXAZEPINE; ALKYNE; ANTIINFECTIVE AGENT; COPPER; HETEROCYCLIC COMPOUND; MOLECULAR SCAFFOLD; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CYCLOADDITION; SYNTHESIS;

BACTERIA (MICROORGANISMS);

EID: 78651387923     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.12.040     Document Type: Article

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63. -1, F(0 0 0) = 552, λ = 0.71073. Data collection yielded 13022 reflections resulting in 1398 unique, averaged reflection, 1351 with I >2σ(I). Full-matrix least-squares refinement led to a final R = 0.0271, wR = 0.0742 and GOF = 1.151. Intensity data were measured on Bruker Smart Apex with CCD area detector.
64. +.
65. General experimental procedure for Cu(I)-catalyzed cycloaddition of azido-alkynes: To a stirred solution of azido-alkyne 1a-k (0.38 mmol) in EtOH (10 mL) was added saturated copper sulfate solution (0.2 mL, 1 M), Cu-turnings (20 mg) and the reaction mixture was refluxed for 12 h. After completion of the reaction (monitored by TLC), the mixture was filtered through celite. The celite pad was washed with ethyl acetate and the combined organic volatiles were removed on a rotary evaporator. The residue was purified by column chromatography over silica gel with ethyl acetate/hexanes (3:7) as eluent to furnish the corresponding [1,2,3] triazolo [5,1-c] [1,4] benzoxazepines, 2a-k.
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