74889-32-0Relevant academic research and scientific papers
Improved one-pot synthesis of 1-aryl-3-trifluoroacetyl-1H-pyrroles under Swern oxidation
Zanatta, Nilo,Aquino, Estefaniada C.,Da Silva, Fabio M.,Bonacorso, Helio G.,Martins, Marcos A. P.
, p. 3477 - 3482,6 (2012/12/12)
This study describes an improved one-pot, four-step synthesis of a new series of 1-aryl-3-trifluoroacetyl pyrroles from the reaction of 3-trifluoroacetyl-4,5-dihydrofuran with arylamines, giving 1,1,1-trifluoro-3-(2- hydroxyethyl)-4-arylamino-3-buten-2-ones, which were directly submitted to Swern oxidation to furnish 1,1,1-trifluoro-3-(2-ethanal)-4-arylamino-3-buten-2-ones. Subsequent intramolecular cyclization of the corresponding enaminoaldehydes followed by aromatization rendered the title compounds in a 30 to 56% overall yield.
Convenient one-pot synthesis of N-substituted 3-trifluoroacetyl pyrroles
Zanatta, Nilo,Wouters, Ana D.,Fantinel, Leonardo,Da Silva, Fabio M.,Barichello, Rosemário,Da Silva, Pedro E. A.,Ramos, Daniela F.,Bonacorso, Helio G.,Martins, Marcos A. P.
experimental part, p. 755 - 758 (2009/07/18)
A new one-pot strategy for the synthesis of a series of new N-substituted 3-trifluoroacetyl pyrroles is presented. These compounds were obtained by the reaction of 3-trifluoroacetyl-4,5-dihydrofuran with primary amines, which generated 1,1,1-trifluoro-3-(2-hydroxyethyl)-4-alkylaminobut-3-en-2-one intermediates. In most cases these intermediates were not stable enough to be isolated. Thus, in the same reaction vessel they were directly submitted to oxidation with PCC (Corey's reagent) to furnish 1,1,1-trifluoro-3-(2-ethanal)-4- alkylaminobut-3-en-2-ones, which under reflux underwent intramolecular cyclization to give the desired N-substituted 3-trifluoroacetyl pyrroles, in moderate yields. All of these pyrroles were tested against pan-susceptible Mycobacterium tuberculosis H37Rv and clinical isolates INH- and RMP-resistant strain and some of these compounds showed significant in vitro antimicrobial activity. Georg Thieme Verlag Stuttgart.
Products from N-Substituted Pyrroles and Trifluoroacetic Anhydride: Ratios and Conformations of Isomers
Chadwick, Derek J.,Meakins, G. Denis,Rhodes, Caroline A.
, p. 878 - 886 (2007/10/02)
A series of N-substituted pyrroles has been treated with trifluoroacetic anhydride.Small alkyl groups or aryl groups (as the N-substituents) lead exclusively, or almost exclusively, to the 2-trifluoroacetyl derivatives, bulky groups (notably 1-adamantyl) to the 3-derivatives, and those of intermediate size (such as i-propyl) to mixtures of isomers.N-Substituted 3-trifluoroacetylpyrroles exist in solution as mixtures of rotational isomers whereas the 2-isomers adopt a preferred conformation in which the nitrogen and oxygen atoms are in the syn orientation.
