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Davis-Beirut reaction: route to thiazolo-, thiazino-, and thiazepino-2H-indazoles.

Farber KM, Haddadin MJ, Kurth MJ - J. Org. Chem. (2014)

Bottom Line: The process consists of formation of the requisite N-(2-nitrobenzyl)(tritylthio)alkylamine, subsequent deprotection of the trityl moiety with TFA, and immediate treatment with aq.KOH in methanol under Davis-Beirut reaction conditions to deliver the target thiazolo-, thiazino-, or thiazepino-2H-indazole in good overall yield.Subsequent S-oxidation gives the corresponding sulfone.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.

ABSTRACT
Methods for the construction of thiazolo-, thiazino-, and thiazepino-2H-indazoles from o-nitrobenzaldehydes or o-nitrobenzyl bromides and S-trityl-protected 1°-aminothioalkanes are reported. The process consists of formation of the requisite N-(2-nitrobenzyl)(tritylthio)alkylamine, subsequent deprotection of the trityl moiety with TFA, and immediate treatment with aq. KOH in methanol under Davis-Beirut reaction conditions to deliver the target thiazolo-, thiazino-, or thiazepino-2H-indazole in good overall yield. Subsequent S-oxidation gives the corresponding sulfone.

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(a) Thiazino and Thiazepino Analogues of 1a. (b) OxazepinoAnalogue of 1c
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sch4: (a) Thiazino and Thiazepino Analogues of 1a. (b) OxazepinoAnalogue of 1c


Davis-Beirut reaction: route to thiazolo-, thiazino-, and thiazepino-2H-indazoles.

Farber KM, Haddadin MJ, Kurth MJ - J. Org. Chem. (2014)

(a) Thiazino and Thiazepino Analogues of 1a. (b) OxazepinoAnalogue of 1c
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4120971&req=5

sch4: (a) Thiazino and Thiazepino Analogues of 1a. (b) OxazepinoAnalogue of 1c
Bottom Line: The process consists of formation of the requisite N-(2-nitrobenzyl)(tritylthio)alkylamine, subsequent deprotection of the trityl moiety with TFA, and immediate treatment with aq.KOH in methanol under Davis-Beirut reaction conditions to deliver the target thiazolo-, thiazino-, or thiazepino-2H-indazole in good overall yield.Subsequent S-oxidation gives the corresponding sulfone.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.

ABSTRACT
Methods for the construction of thiazolo-, thiazino-, and thiazepino-2H-indazoles from o-nitrobenzaldehydes or o-nitrobenzyl bromides and S-trityl-protected 1°-aminothioalkanes are reported. The process consists of formation of the requisite N-(2-nitrobenzyl)(tritylthio)alkylamine, subsequent deprotection of the trityl moiety with TFA, and immediate treatment with aq. KOH in methanol under Davis-Beirut reaction conditions to deliver the target thiazolo-, thiazino-, or thiazepino-2H-indazole in good overall yield. Subsequent S-oxidation gives the corresponding sulfone.

Show MeSH
Related in: MedlinePlus