Facile Synthesis of 2,5‐Diarylthiazoles via Palladium‐Catalyzed Tandem C—H Substitutions. Design of Tunable Light Emission and Liquid Crystalline Characteristics.

Mori, Akira; Sekiguchi, Akitoshi; Masui, Kentaro; Shimada, Tomohiro; Horie, Masaaki; Osakada, Kozo; Kawamoto, Masuki; Ikeda, Tomiki

doi:10.1002/chin.200322120

Cited by 5 publications

(7 citation statements)

References 2 publications

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“…13 C{ 1 H} NMR (CDCl 3 , 100 MHz): δ (ppm) 148.5, 138.9, 131.7, 128.5, 128.2, 122.7, 122.3, 114.4, 84.4, 84.0, 22.7 7, 138.6, 131.7, 129.0, 122.6, 119.4, 84.6, 83.5, 22.8, 21.4. MS (EI, 70 eV; m/z (relative intensity)): 279 ([M + 1], 20), 278 (100), 207 (20), 128 (15), 115 (23), 91 (14). HRMS: calcd for C 17 H 15 N 2 S (ESI-TOF, [M + H] + ), 279.0956; found, 279.0948.…”

Section: -((3-phenylprop-2-yn-1-yl)thio)-1h-benzo[d]imidazole (1a) 17bmentioning

confidence: 99%

“…9, 148.7, 133.2, 122.6, 114.7, 114.0, 84.5, 82.8, 55.3, 22.9. MS (EI, 70 eV; m/z (relative intensity)): 295 ([M + 1], 19), 294 (100), 207 (23), 192 (10), 103 (20), 77 (13) 4, 139.3, 130.8 (q, J = 32.3 Hz), 128.7, 128.4 (q, J = 3.9 Hz), 124.9 (q, J = 3.3 Hz), 123.7 (q, J = 273.0 Hz), 122.2, 114.4, 85.8, 82.7, 25.5. MS (EI, 70 eV; m/z (relative intensity)): 333 ([M + 1], 21), 332 (100), 331 (23), 187 (23), 134 (17), 102 (21).…”

Section: -((3-(4-methoxyphenyl)prop-2-yn-1-yl)thio)-1h-benzo[d]imidaz...mentioning

confidence: 99%

“…19 In addition, many heterocycles having a thiazole group in the molecule present structural and electronic properties. 20 The main improvement of our methodology is the use of diorganyl diselenides to both promote the cyclization and functionalize the new heterocycles. It provides a useful and valuable method for further functionalization by using the peculiar reactivity of the Csp 2 −selenium bond.…”

Section: ■ Introductionmentioning

confidence: 99%

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Cyclization of Thiopropargyl Benzimidazoles by Combining Iron(III) Chloride and Diorganyl Diselenides

Goulart¹,

Kazmirski²,

Back

et al. 2019

J. Org. Chem.

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A practical synthetic approach to the synthesis of 3-(organoselenyl)-imidazothiazines was developed. The methodology involved the regioselective 6-endo-dig cyclization of thiopropargyl benzimidazoles promoted by diorganyl diselenides and iron(III) chloride. The investigation to determine the best reaction conditions indicated the use of thiopropargyl benzimidazoles (0.25 mmol) with diorganyl diselenides (1.0 equiv) and iron(III) chloride (2.0 equiv) in dichloromethane at 40 °C for 30 min to be optimal. Under these conditions, the scope of the substrates was evaluated varying the structures of thiopropargyl benzimidazoles and diorganyl diselenides giving 28 3-(organoselenyl)-imidazothiazines in moderate to good yields. The reaction conditions were also applicable to diorganyl ditellurides; however, they did not work for diorganyl disulfides. The mechanism studies were carried out indicating that the cyclization proceeds via a cooperative action of diorganyl diselenides and iron(III) chloride, but a direct electrophilic cyclization, promoted by the in situ formed electrophilic organoselenium species, cannot be ruled out.

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Section: -((3-phenylprop-2-yn-1-yl)thio)-1h-benzo[d]imidazole (1a) 17bmentioning

confidence: 99%

Section: -((3-(4-methoxyphenyl)prop-2-yn-1-yl)thio)-1h-benzo[d]imidaz...mentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Cyclization of Thiopropargyl Benzimidazoles by Combining Iron(III) Chloride and Diorganyl Diselenides

Goulart¹,

Kazmirski²,

Back

et al. 2019

J. Org. Chem.

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“…The C − H substitution reaction of thiazole by the catalysis of the palladium/ copper system is carried out in the presence of tetrabutylammonium fluoride under mild conditions. Various 2,5-diarylthiazole derivatives (2.6.1) were synthesized in good yields [51] (Figure 11).…”

Section: Miscellaneous Methodsmentioning

confidence: 99%

“…The interest in the synthesis of compounds containing the thiazole moiety has been increasing steadily in view of their utility in the field of photosensitizers, rubber vulcanization [2], liquid crystals [3,4], sensors [5], sunscreens [6], catalysts [7], dyes [8], pigments [1], and chromophores [9,10]. Moreover, thiazoles occupy a prominent place in current medicinal chemistry due to their wide range of applications in the field of drug design and discovery [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Thiazole Derivatives

Ibrahim¹,

Rizk²

2021

Azoles - Synthesis, Properties, Applications and Perspectives

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Thiazoles belong to the group of azole heterocycles. They are aromatic five-membered heterocycles containing one sulfur and one nitrogen atom. In recent years thiazoles, their derivatives, and isomers have gained considerable attention because of their broad applications in different fields, such as agrochemicals, industrial, and photographic sensitizers. Also, they have pharmaceutical and biological activities that include antimicrobial (sulfazole), antiretroviral (ritonavir), antifungal (abafungin), anticancer (tiazofurin), antidiabetic, anti-inflammatory, anti-Alzheimer, antihypertensive, antioxidant, and hepatoprotective activities. The compounds containing thiazole moieties are a prominent structural feature in a variety of natural products, such as vitamin B and penicillin. Thus, in this chapter several types of thiazole-based heterocyclic scaffolds such as monocyclic or bicyclic systems synthesis and their biological activities studies are presented. Furthermore modification of thiazole-based compounds at different positions to generate new molecules with potent antitumor, antioxidant, and antimicrobial activities is described.

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Direct (Hetero)arylation Polymerization: Simplicity for Conjugated Polymer Synthesis

et al. 2016

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Direct (hetero)arylation polymerization (DHAP) has recently been established as an environmentally benign method for the preparation of conjugated polymers. This synthetic tool features the formation of C-C bonds between halogenated (hetero)arenes and simple (hetero)arenes with active C-H bonds, thereby circumventing the preparation of organometallic derivatives and decreasing the overall production cost of conjugated polymers. Since its inception, selectivity and reactivity of DHAP procedures have been improved tremendously through the careful scrutinity of polymerization outcomes and the fine-tuning of reaction conditions. A broad range of monomers, from simple arenes to complex functionalized heteroarenes, can now be readily polymerized. The successful application of DHAP now leads to nearly defect-free conjugated polymers possessing comparable, if not slightly better, characteristics than their counterparts prepared using classical cross-coupling methods. This comprehensive review describes the mechanisms involved in this process from experimental and theoretical standpoints, presents an up-to-date compendium of materials obtained by this means, and exposes its current limitations and challenges.

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Facile Synthesis of 2,5‐Diarylthiazoles via Palladium‐Catalyzed Tandem C—H Substitutions. Design of Tunable Light Emission and Liquid Crystalline Characteristics.

Cited by 5 publications

References 2 publications

Cyclization of Thiopropargyl Benzimidazoles by Combining Iron(III) Chloride and Diorganyl Diselenides

Cyclization of Thiopropargyl Benzimidazoles by Combining Iron(III) Chloride and Diorganyl Diselenides

Synthesis and Biological Evaluation of Thiazole Derivatives

Direct (Hetero)arylation Polymerization: Simplicity for Conjugated Polymer Synthesis

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