A Convenient Route to 1‐Alkyl‐5‐trifluoromethyl‐1, 2, 3‐triazole‐4‐carboxylic Acids Employing a Diazo Transfer Reaction. Issue 14 (3rd April 2013)

• Record Type: Journal Article
• Authors: Iminov, Rustam T.; Mashkov, Alexander V.; Chalyk, Bohdan A.; Mykhailiuk, Pavel K.; Tverdokhlebov, Anton V.; Tolmachev, Andrey A.; Volovenko, Yulian M.; Shishkin, Oleg V.; Shishkina, Svetlana V.
• Is Part Of: European journal of organic chemistry. Issue 14(2013)
• Page Start: 2891
• Page End: 2897
• Publication Date: 2013-04-03
• Subjects: Synthetic methods -- Medicinal chemistry -- Nitrogen heterocycles -- ­Amines -- Azides -- Fluorine; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300030
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The reaction of ethyl 3‐(alkylamino)‐4, 4, 4‐trifluoro‐but‐2‐enoates with mesyl azide in the presence of 1, 8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) gave ethyl 1‐alkyl‐5‐trifluoromethyl‐1, 2, 3‐triazole‐4‐carboxylates in good yields. Further hydrolysis of the ester group afforded the title compounds on a multigram scale. Abstract : A multigram‐scale synthesis of 1‐alkyl‐5‐trifluoromethyl‐1, 2, 3‐triazole‐4‐carboxylic acids has been developed. The triazole ring formation by means of a diazo transfer reaction with mesyl azide was the key step.