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Volumn 6, Issue 8, 2008, Pages 1364-1376

Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles

Author keywords

[No Author keywords available]

Indexed keywords

AZIDOACRYLATE INTERMEDIATES; PYRIDINE RING; SOLVENT-DEPENDENT OXIDATIONS;

EID: 41549104168     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b719776d     Document Type: Article
Times cited : (8)

References (54)
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    • 1H NMR of the crude product and estimated to be 95:5 For a study on the ortho-directing properties of tetrahydropyranyl ethers of 3- and 4-hydroxypyridines during metalation reactions, see:
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    • 1H NMR of the white solid which was obtained after quenching the reaction at -20 °C with ice, warming up to 4 °C over 1 h (in a refrigerator) and filtration of the resulting precipitate on a 0.45 μm glass fiber membrane For leading references on hypervalent iodine(iii) reagents, see:
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  • 43
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    • It should be noted that a low yield (19%) of compound 12a was obtained using 3 equivalents of cerium ammonium nitrate (CAN) in an acetonitrile-water medium Atom distances: C(6)-O(2): 1.210(3) å; C(8)-O(4): 1.213(3) å; C(10)-O(1): 1.203(4) å; N(3)-H(2): 0.88 å Atom distances: C(6)-O(2): 1.210(3) å; C(8)-O(4): 1.213(3) å; C(10)-O(1): 1.203(4) å; N(3)-H(2): 0.88 å
    • H. Tohma H. Morioka Y. Harayama M. Hashizume Y. Kita Tetrahedron Lett. 2001 42 6899
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    • During our investigations on the demethylation of dimethoxy 5- and 6-azaindoles, another research group has described selective monodemethylations of dimethoxy-6-azaindoles:
    • X. Chen J. Zhu Angew. Chem., Int. Ed. 2007 46 3962
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    • Oxidation reactions with PIFA were carried out in open vessels, using non-degassed solvents It is noteworthy that the PIFA-mediated (4 equiv) oxidation reaction of dimethoxyazaindoles 2 in methanol-acetonitrile did not lead to the formation of functionalised azaindoles 17
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