Reactions of 5-[3-(trifluoromethyl)-phenyl]furan-2-carbaldehyde

Abstract

Keywords: methyl 2-[3-(trifluoromethyl)phenyl)]-4H-furo[3,2-b]pyrrole-5-carboxylate, 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde, 2-[3-(trifluoromethyl)phenyl)]furo[3,2-c]pyridine, Knoevenagel reaction.During the past few decades many results have been published in the field of synthesis and study of physical and chemical properties of heterocyclic compounds containing a furan ring connected or fused with a benzene ring or with different heterocyclic systems.Substituted furans are ubiquitous structural units in natural products and pharmaceuticals [1] and have been widely used as synthetic intermediates [2,3]. Many of the published condensation products are biologically active compounds [4,5] or can be used as intermediates in organic synthesis [6][7][8][9].In the past two decades one of us was interested in the syntheses, reaction, and aromaticity of variously substituted furo[3,2-b]pyrroles and their [2,3-b]-isomers [10,11]. Substitution, addition, and cycloaddition reactions of furo[3,2-b]pyrroles and their condensed derivatives involving the interesting transformations of furo[3,2-b]pyrrole system were presented. We also reported on the synthesis of 2-arylfuro[3,2-c]pyridines [12, 13] and 2,3-dimethylfuro[3,2-c]pyridine [14]. Later on some furo[3,2-c]pyridines have been used for the preparation of Cu(II) and Ni(II) complexes [15]. Furo[3,2-c]pyridine and its 2-methyl-, 2,3-dimethyl-and benzo [4,5] derivative were used for the first time as ligands to synthesize potentially new Werner clathrates, and the structural characterization, spectral, and magnetic properties of isothiocyanate nickel(II) complexes were published [16,17].

2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions

“…was made by thermolysis of the corresponding methyl 2-azido-3-{5-[3-(trifluoromethyl)phenyl]-2-furyl}propenoate, which was formed by condensation of 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde with methyl azido acetate, where sodium methoxide was used as a catalyst [28]. Compounds 1b,c were formed by reaction with 1a using methyl iodide or benzyl chloride under conditions of phase transfer catalysis (PTC) (Scheme 1).…”

Synthesis, Complex Compounds and Antimicrobial Activity of Some Derivatives of Furo[3,2-C]Pyridine and Their Starting Compounds

“…The acids 1b-1d were synthesized by condensation of the appropriate carbaldehyde with malonic acid under Knoevenagel conditions. The compounds 4b-4f were prepared analogously by cyclisation of appropriated azides (SLEZIAK and KRUTOŠÍKOVÁ, 1996;GAJDOŠ et al, 2006;MOJUMDAR et al, 2009) Reaction of 4b and 4d with phosphorus pentasulfide led to corresponding thiones 5a, 5b, which were methylated in PTC conditions giving 6a and 6b (BRADIAKOVÁ et al, 2009;TARABOVÁ et al, 2010). 2-Methyl[1]benzofuro[3,2-c]pyridine-1-one (4e) and 5-metyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine-4(5H)-one (4f) were obtained by reaction of 4b, 4d with NaH and then methylated with methyl iodide.…”

“…Analogously were synthesized chloroderivatives 7b-7d and they are described in ref. (SLEZIAK and KRUTOŠÍKOVÁ, 1996;BRADIAKOVÁ et al, 2008;GAJDOŠ et al, 2006) Refluxing of appropriate chloroderivatives 7b and 7d with secondary heterocyclic amines gave 8a-8d (BRADIAKOVÁ et al, 2009;MOJUMDAR et al, 2009). The compounds 8f-8j were prepared according (TARABOVÁ et al, 2010;BRADIAKOVÁ et al, 2009;BENCKOVÁ and KRUTOŠÍKOVÁ 1999).…”

“…For a long time we have been interested in studying of the synthesis and reactivity of various furo[3,2-c]pyridines (BOBOŠÍK et al, 1995;KRUTOŠÍKOVÁ and SLEZIAK 1996;MOJUMDAR et al, 2005;GAJDOŠ et al, 2006;BÚDOVÁ et al, 2006;BRADIAKOVÁ et al, 2008;TARABOVÁ et al, 2010). This type of the fused heterocycles can be readily coordinated to metal centers through N-donor atom.…”

Microwave assisted reactions of 2-[3-(Trifluoromethyl)phenyl]-4-R1-furo[3,2-b] pyrrole-5-carboxhydrazides

“…The present study is a follow-up paper to our previous research, dealing with the synthesis and reactions of furo [3,2-b]pyrrole system [11,12] and the study on the effect of microwave irradiation on its reactions with heterocyclic aldehydes [13][14][15].…”