Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2H-indazoles

[Image: see text] 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,...

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Autores principales: Farber, Kelli M., Haddadin, Makhluf J., Kurth, Mark J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120971/
https://www.ncbi.nlm.nih.gov/pubmed/25019525
http://dx.doi.org/10.1021/jo501014e
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author Farber, Kelli M.
Haddadin, Makhluf J.
Kurth, Mark J.
author_facet Farber, Kelli M.
Haddadin, Makhluf J.
Kurth, Mark J.
author_sort Farber, Kelli M.
collection PubMed
description [Image: see text] 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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spelling pubmed-41209712015-07-14 Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2H-indazoles Farber, Kelli M. Haddadin, Makhluf J. Kurth, Mark J. J Org Chem [Image: see text] 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. American Chemical Society 2014-07-14 2014-08-01 /pmc/articles/PMC4120971/ /pubmed/25019525 http://dx.doi.org/10.1021/jo501014e Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Farber, Kelli M.
Haddadin, Makhluf J.
Kurth, Mark J.
Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2H-indazoles
title Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2H-indazoles
title_full Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2H-indazoles
title_fullStr Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2H-indazoles
title_full_unstemmed Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2H-indazoles
title_short Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2H-indazoles
title_sort davis–beirut reaction: route to thiazolo-, thiazino-, and thiazepino-2h-indazoles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120971/
https://www.ncbi.nlm.nih.gov/pubmed/25019525
http://dx.doi.org/10.1021/jo501014e
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AT kurthmarkj davisbeirutreactionroutetothiazolothiazinoandthiazepino2hindazoles

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