Davis-Beirut reaction: Route to thiazolo-, thiazino-, and thiazepino-2 h -indazoles
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American Chemical Society
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. © 2014 American Chemical Society.
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Benzaldehydes, Benzyl compounds, Indazoles, Molecular structure, Oxidation-reduction, Thiazines, Thiazoles, Chemistry, Organic compounds, 10 chloro 3,4 dihydro 2h [1,3]thiazino[3,2 b]indazole, 2 (1 hydroxypropan 2 yl)isoindoline 1,3 dione, 2 (1 iodopropan 2 yl)isoindoline 1,3 dione, 2 [1 (tritylthio)propan 2 yl]isoindoline 1,3 dione, 2,3 dihydrothiazolo[3',2':1,5]pyrazolo[4,3 b]pyridine, 2,3 dihydrothiazolo[3,2 b]indazole, 2,3 dihydrothiazolo[3,2 b]indazole 1,1 dioxide, 2,3,4,5 tetrahydro [1,3]oxazepino[3,2 b]indazole, 2,3,4,5 tetrahydro [1,3]thiazepino[3,2 b]indazole, 2,3,4,5 tetrahydro [1,3]thiazepino[3,2 b]indazole 1,1 dioxide, 3 methyl 1 (tritylthio)butan 2 amine, 3 methyl 2,3 dihydrothiazolo[3,2 b]indazole, 3,4 dihydro 2h pyrido[3',2':3,4]pyrazolo[5,1 b][1,3]thiazine, 3,4 dihydro 2h [1,3]thiazino[3,2 b]indazole, 3,4 dihydro 2h [1,3]thiazino[3,2 b]indazole 8 carboxylic acid, 3,4 dihydro-2 h [1,3]thiazino[3,2 b]indazole 1,1 dioxide, 7,8 dihydro [1,3]dioxolo[4,5 f ]thiazolo[3,2 b]indazole, 7,8 dihydro [1,3]dioxolo[4,5 f ]thiazolo[3,2 b]indazole 9,9 dioxide, 7,8,9,10 tetrahydro [1,3]dioxolo[4,5 f][1,3]thiazepino[3,2 b]indazole, 8,9 dihydro 7h [1,3]dioxolo[4,5 f ][1,3]thiazino[3,2 b] indazole 10,10 dioxide, 8,9 dihydro 7h [1,3]dioxolo[4,5 f ][1,3]thiazino[3,2 b]indazole, 8,9 dimethoxy 3,4 dihydro 2h [1,3]thiazino[3,2 b]indazole, 9 bromo 3,4 dihydro 2h [1,3]thiazino[3,2 b]indazole, Benzaldehyde derivative, Benzo[4,5]thiazolo[3,2 b]indazole, Bromine derivative, Indazole derivative, Mercaptamine, Sulfone, Unclassified drug, Unindexed drug, Benzyl derivative, Thiazine derivative, Thiazole derivative, 2-nitrobenzyl, Alkylamine, Deprotection, Indazole, Nitrobenzyl bromides, Reaction conditions, Amination, Article, Chemical reaction, Davis beirut reaction, Electrophilicity, Liquid chromatography, Mass spectrometry, Oxidation, Reaction time, Stereospecificity, Chemical structure, Oxidation reduction reaction, Synthesis, Potassium hydroxide