Microwave-assisted synthesis of fused heterocycles incorporating trifluoromethyl moiety

Shaaban, Mohamed R.

doi:10.1016/j.jfluchem.2008.09.002

Cited by 37 publications

(13 citation statements)

References 46 publications

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“…Furthermore, compound 2 was reacted with diethyl ethoxymethylenemalonate either by heating in water under reflux or by fusion. The reaction mechanism [40] was assumed to proceed via two mechanistic pathways (Route A and Route B, Fig. 1) involving the nucleophilic substitution of the ethoxy function either by the exocyclic amino group leading to the acyclic analogue 13, followed by intramolecular cyclization via elimination of another ethanol moiety leading to the dihydrotriazolopyrimidinone 11 (Route A) or via the endocyclic secondary amino group followed by intramolecular cyclization (Route B) to yield the dihydrotriazolopyrimidinone 12.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Anticancer Evaluation of Some Novel 5‐Amino[1,2,4]Triazole Derivatives

Hassan

Sarg

Bayoumi

et al. 2018

Journal of Heterocyclic Chem

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Novel [1,2,4]triazole derivatives were synthesized via various synthetic pathways. Among which were different substituted [1,2,4]triazole analogues that were synthesized, in addition to various fused [1,2,4]triazolo[1,5‐a]pyrimidine derivatives, [1,2,4]triazolo[1,5‐a][1,3,5]triazines, and [1,2,4]triazolo[5,1‐c][1,2,4]triazines. Besides, benzo[h][1,2,4]triazolo[5,1‐b]quinazolines, [1,2,4]triazolo‐[5,1‐b]quinazoline, [1,2,4]triazolo[1,5‐a]quinazoline and [1,2,4]triazolo[5,1‐d][1,2,3,5]tetrazine derivatives were also synthesized. The newly synthesized compounds were evaluated for their in vitro anticancer activity against liver cancer HepG2 and breast cancer MCF7 cell lines compared with the reference drug doxorubicin. Compounds 4, 7, 15, 17, 28, 34, and 47 were found to exert promising anticancer activity against HepG2 cell line showing IC50 values ranging from 17.69 to 25.4 μM/L, while compounds 7, 14a, 17, 28, and 34 showed significant activity against MCF7 cell line with IC50 values ranging from 17.69 to 27.09 μM/L.

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Section: Resultsmentioning

confidence: 99%

“…Amino-3-(4-chlorophenyl)-1H-[1,2,4]triazol-1-yl)(4chlorophenyl)methyl]-3,4-dihydronaphthalen-1(2H)-one(40). Yellow crystals, 0.15 g (33%); mp 255-257°C.…”

mentioning

confidence: 99%

Synthesis and Anticancer Evaluation of Some Novel 5‐Amino[1,2,4]Triazole Derivatives

Hassan

Sarg

Bayoumi

et al. 2018

Journal of Heterocyclic Chem

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“…The latter were formed from intermediates A by the endocyclic nitrogen atom of pyrazole attacking the carbonyl group at fluorinated substituent [136]. The interaction of pyrazole-3(5)-diazonium salt 1 with 4,4,4-trifluoro-1-(thiophen-2-yl)butan-1,3-dione (64) occurred under microwave irradiation in pyridine and gave the pyrazolotriazines 65 [137]. The hetaryl ketones 66а,b also were smoothly coupled to pyrazole diazonium salts 1.…”

Section: Intermolecular Azo Couplingmentioning

confidence: 99%

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

Ledenyova

Didenko

Shikhaliev

2014

Chem Heterocycl Comp

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The methods of synthesis, structure, reactivity, and synthetic utility of pyrazole-3(5)-diazonium salts are reviewed here for the first time, with emphasis on heterocyclization reactions of these compounds.More than one hundred years have passed since α-diazo derivatives of pyrazole were discovered. A substantial amount of knowledge has been accumulated over this time regarding the stability, structure, and transformations of these compounds. However, the chemistry of pyrazole-3(5)-diazonium salts developed rapidly only in the second half of the 20th century, with many studies performed in various countries, in particular Germany, Egypt, Russia, and Japan. Unfortunately, no systematic review has been compiled for the wide range of data about pyrazole-3(5)-diazonium salts. Some aspects regarding the properties of these compounds have been discussed in reviews and monographs on other topics [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17].

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“…Further, all our attempts to improve the yield at elevated temperature and longer reaction times were unsuccessful (Scheme 9). [43][44][45][46] The condensation of aldehyde with various derivatives of 4-amino-5-aryl-4H-1,2,4-triazole 3-thiol either by using microwave irradiation in the presence of Montmorillonite K-10 clay in DMSO [47] or by traditional method, [48] [49,50] Ball et al [51] developed a rapid synthesis of unprecedented [1,3] Shaaban [52] has synthesized 6-thienoyl-7-(trifluoromethyl)- [1,2,4]triazolo [4,3-a]pyrimidine in 91% yields (and 6-thienoyl-7-(trifluoromethyl)benzimidazo[1,2-a]pyrimidine in 83% yields) by MW irradiation of 4,4,4-trifluoro-1-(thien-2-yl)butane 1,3-dione, 3-amino-1,2,4-triazole (or 2-aminobenzimidazole), and triethylorthoformate at 100 °C for 5 min (Scheme 13). Most of the thermal syntheses of such compounds consume a lot of time and/or lack of high selectivity.…”

Section: Synthesis Of 124-triazolesmentioning

confidence: 99%

Role of Microwaves in the Synthesis of Fused Five-Membered Heterocycles with Three N-Heteroatoms

Kaur

2014

Synthetic Communications

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The development of new strategies for the synthesis of small-sized heterocycles has remained a highly attractive but challenging proposition. An overview of the application of microwave irradiation in three nitrogen atoms containing fused five membered heterocyclic compounds synthesis is presented, focusing on the developments in the last 5-10 years. This contribution covers the literature concerning the total synthesis of N,N,N-heterocycles. The literature data are summarized based on the type of cycles.

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Microwave-assisted synthesis of fused heterocycles incorporating trifluoromethyl moiety

Cited by 37 publications

References 46 publications

Synthesis and Anticancer Evaluation of Some Novel 5‐Amino[1,2,4]Triazole Derivatives

Synthesis and Anticancer Evaluation of Some Novel 5‐Amino[1,2,4]Triazole Derivatives

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

Role of Microwaves in the Synthesis of Fused Five-Membered Heterocycles with Three N-Heteroatoms

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