Literature DB >> 19936959

A p-methoxybenzyl (PMB) protection/deprotection approach toward the synthesis of 5-phenoxy-4-chloro-N-(aryl/alkyl) thiophene-2-sulfonamides.

Alfred L Williams1, Srinivasa R Dandepally, Sharadsrikar V Kotturi.   

Abstract

The synthesis of 17 phenoxy substituted 4-chloro-N-(aryl/alkyl)thiophene-2-sulfonamides using a PMB protection/deprotection strategy is described. Nucleophilic displacement of p-methoxybenzyl (PMB) protected 4,5-dichloro-N-(aryl/alkyl)-thiophene-2-sulfonamides was carried out with different phenols under mild basic conditions. Reaction times of 3-6 h and overall yields of 78-98% were achieved with the PMB group in place compared to no reaction without this protecting group. The PMB group was easily and selectively removed in 68-98% yield using TFA in DCM.

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Year:  2009        PMID： 19936959     DOI： 10.1007/s11030-009-9208-y

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  14 in total

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Authors:  Andrew G Cole; Axel Metzger; Marc-Raleigh Brescia; Lan-Ying Qin; Kenneth C Appell; Christopher T Brain; Allan Hallett; Pam Ganju; Alastair A Denholm; James R Wareing; Timothy J Ritchie; Gillian M Drake; Stuart J Bevan; Aisling MacGloinn; Andrew McBryde; Viral Patel; Paul J Oakley; Ximena Nunez; Hubert Gstach; Peter Schneider; John J Baldwin; Roland E Dolle; Edward McDonald; Ian Henderson
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10.  An insight into the pharmacophores of phosphodiesterase-5 inhibitors from synthetic and crystal structural studies.

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Journal:  Biochem Pharmacol       Date:  2008-02-12       Impact factor: 5.858
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