Davis–Beirut Reaction: Route to Thiazolo‑, Thiazino‑, and Thiazepino‑2H‑indazoles
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 depr...
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| Veröffentlicht in: | Journal of organic chemistry 2014-08, Vol.79 (15), p.6939-6945 |
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| container_issue | 15 |
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| container_title | Journal of organic chemistry |
| container_volume | 79 |
| creator | Farber, Kelli M Haddadin, Makhluf J Kurth, Mark J |
| description | 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. |
| doi_str_mv | 10.1021/jo501014e |
| format | Article |
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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. 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Org. Chem</addtitle><date>2014-08-01</date><risdate>2014</risdate><volume>79</volume><issue>15</issue><spage>6939</spage><epage>6945</epage><pages>6939-6945</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><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.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25019525</pmid><doi>10.1021/jo501014e</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2014-08, Vol.79 (15), p.6939-6945 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Benzaldehydes - chemical synthesis Benzaldehydes - chemistry Benzyl Compounds - chemical synthesis Benzyl Compounds - chemistry Indazoles - chemical synthesis Indazoles - chemistry Molecular Structure Oxidation-Reduction Thiazines - chemical synthesis Thiazines - chemistry Thiazoles - chemical synthesis Thiazoles - chemistry |
| title | Davis–Beirut Reaction: Route to Thiazolo‑, Thiazino‑, and Thiazepino‑2H‑indazoles |
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