Convergent procedure for the synthesis of trifluoromethyl-containing N-(pyridinyl-triazolyl)pyrimidin-2-amines

Bonacorso, Hélio G.; Bortolotto, Guilherme P.; Navarini, Jussara; Porte, Liliane M. F.; Wiethan, Carson W.; Zanatta, Nilo; Martins, Marcos A. P.; Flores, Alex F. C.

doi:10.1016/j.jfluchem.2010.08.002

Cited by 13 publications

(8 citation statements)

References 45 publications

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“…Until recently, only a limited number of methods have been described for the synthesis of trifluoromethylated pyrimidines by using readily available materials . Previously, the preparation of mono‐, di‐, and trifluoromethylated pyrimidines from fluorinated 1,3‐diketones, enones, and aminoenones as well as β‐alkoxyvinyl(perfluoroalkyl)ketones, perfluoroalkyl β‐diketo phosphorus ylides, and propargylic fluorides were also reported.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF₃‐Ynones

et al. 2017

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A highly efficient synthetic method for the preparation of of 6‐trifluoromethylated pyrimidines was developed. The reaction of CF3‐substituted ynones and nitrogen 1,3‐bis(nucleophile)s was employed for the one‐pot assembly of the pyrimidine core. The cascade route proceeded through an aza‐Michael addition, intramolecular cyclization, and dehydration reaction sequence to give the target heterocycles in excellent yields (up to 97 %). When acetamidine was used as the bis(nucleophile), the unexpected addition of two equivalents of the CF3‐substituted ynone to the acetamidine was observed.

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Section: Introductionmentioning

confidence: 99%

One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF₃‐Ynones

et al. 2017

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“…The structures of the synthesized secondary amines 3a-3j were identified by one-and two-dimensional NMR experiments, with their spectral signals being assigned by comparison with other pyrimidines synthesized in our laboratory [24] and by data already described in the literature for benzimidazoles [15].…”

Section: Resultsmentioning

confidence: 99%

“…In 2008, we reported the syntheses of a series of N-(pyridinyl-triazolyl)pyrimidin-2-amines from the cyclocondensation reaction of N-[5-(pyridinyl)-1H-1,2,4-triazol-3-yl]guanidine with 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones [24], which were done in ethanol under reflux for 18 h and resulted in yields of 40-68 %.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthetic access to novel N-(Pyrimidinyl)-N-(1H-benzo[d]imidazolyl)amines in an aqueous medium

et al. 2015

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This study describes a simple, efficient, and environmentally benign procedure for synthesizing a novel series of 13 N-(pyrimidinyl)-N-(1H-benzo[d]imidazolyl) amines, from the cyclocondensation reaction of (benzo[d]-imidazolyl)guanidine with 4-alkoxy-4-alkyl(aryl/ heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones or 2,2,2-trifluoro-1-(2-methoxycyclohexen-1-en-1-yl)ethanone. The (benzo[d]-imidazolyl)guanidine precursor was earlier obtained from the reactions of cyanoguanidine with o-phenylenediamine. The trifluoroacetylated enol ethers were synthesized from the trifluoroacetylation reaction of enol ethers or acetals with trifluoroacetic anhydride. The main reactions were performed in pure refluxing water as the solvent (1-24 h), without catalysts, and the corresponding new N-(pyrimidinyl)-N-(1H-benzo[d]imidazolyl)amines were obtained at good to excellent yields (60-90 %). Subsequently, N-alkylation reactions were performed to obtain tertiary amines and to increase the solubility of the amines. Graphical abstract

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“…: m/z (%) = 390 (100, M + ), 360 (37), 344 (19), 332 (19), 314 (14), 299 (12), 298 (61), 297 (37), 286 (22), 285 (12), 176 (11), 127 (10), 115 (14), 103 (10), 102 (36), 101 (20), 100 (13), 77 (15), 76 (36), 75 (33), 74 (14), 69 (33), 63 (11), 51 (24), 50 (24), 44 (48), 43 (14).…”

Section: Ms (Ei)mentioning

confidence: 99%

“…9 In contrast, only a very limited number of methods for the synthesis of trifluoromethylated pyrimidines have been described previously. 10 All these methods are based on the use of fluorinated building blocks such as 1,3-diketones, 11 -alkoxyvinyl(perfluoroalkyl)ketones, 12 enones, 13 aminoenones, 14 and perfluoroalkyl -diketo phosphorus ylides. 15 However, the majority of these methods suffer from one or more disadvantages, which include harsh reaction conditions (high temperatures, long reaction times, transition metal usage as a catalyst), hard-to-reach starting materials, and moderate yields.…”

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confidence: 99%

Reaction of Bromoenones with Amidines: A Simple Catalyst-Free Approach to Trifluoromethylated Pyrimidines

Romanov

Rulev

Popov³

et al. 2020

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A facile one-pot synthesis of trifluoromethylated pyrimidines has been achieved by the treatment of fluorinated 2-bromoenones with aryl- and alkylamidines. The assembly of pyrimidine core proceeds by the cascade reactions via aza-Michael addition–intramolecular cyclization–dehydrohalogenation/dehydration sequence. This strategy is featured by high selectivity and mild reaction conditions giving the target heterocycles in high yields (up to 99%). The unique influence of trifluoromethyl group on the reaction path is demonstrated.

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Convergent procedure for the synthesis of trifluoromethyl-containing N-(pyridinyl-triazolyl)pyrimidin-2-amines

Cited by 13 publications

References 45 publications

One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF₃‐Ynones

One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF₃‐Ynones

Efficient synthetic access to novel N-(Pyrimidinyl)-N-(1H-benzo[d]imidazolyl)amines in an aqueous medium

Reaction of Bromoenones with Amidines: A Simple Catalyst-Free Approach to Trifluoromethylated Pyrimidines

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Convergent procedure for the synthesis of trifluoromethyl-containing N-(pyridinyl-triazolyl)pyrimidin-2-amines

Cited by 13 publications

References 45 publications

One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF3‐Ynones

One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF3‐Ynones

Efficient synthetic access to novel N-(Pyrimidinyl)-N-(1H-benzo[d]imidazolyl)amines in an aqueous medium

Reaction of Bromoenones with Amidines: A Simple Catalyst-Free Approach to Trifluoromethylated Pyrimidines

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One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF₃‐Ynones

One‐Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF₃‐Ynones