A metal-free and recyclable synthesis of benzothiazoles using thiourea as a sulfur surrogate

Yin, Yan; Zhou, Hong; Liu, Xichen; Chen, Haiying; Wu, Fanhong; Zhang, Heng; Tao, Ruiheng; Cheng, Fengkai; Feng, Yangbo

doi:10.1016/j.tetlet.2015.02.054

Cited by 4 publications

(4 citation statements)

References 14 publications

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“…A white precipitate was formed, which was isolated by centrifugation and washed extensively with water to give the product as white crystals (36.0 mg, 233 μmol, 99%): 1 H NMR (500 MHz, CDCl 3 , 298 K) δ 7.17 (d, J = 8.6 Hz, 2H), 6.85 (d, J = 8.6 Hz, 2H), 3.80 (s, 3H), 3.59 (s, 2H); 13 C NMR (126 MHz, CDCl 3 , 298 K) δ 159.2, 130.7, 129.6, 114.0, 55.4, 42.9. The analytical data are in accordance with the literature …”

Section: Methodsmentioning

confidence: 99%

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Benzylic Thio and Seleno Newman–Kwart Rearrangements

et al. 2018

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The thermally induced O → S and O → Se migration reactions facilitate the rearrangement of O-benzyl thio- and selenocarbamates [BnOC(═X)NMe] (X = S or Se) into their corresponding S-benzyl thio- and Se-benzyl selenocarbamates [BnXC(═O)NMe] (X = S or Se). A series of substituted O-benzyl thio- and selenocarbamates were synthesized and rearranged in good yields of 33-88%. The reaction rates are higher for substrates with electron-donating groups in the 2 or 4 position of the aromatic ring, but the rearrangement also proceeds with electron-withdrawing substituents. The rearrangement follows first-order reaction kinetics and proceeds via a tight ion pair intermediate consisting of the benzylic carbocation and the thio- or selenocarbamate moiety. Computational studies support these findings.

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Section: Methodsmentioning

confidence: 99%

“…The analytical data are in accordance with the literature. 49 1,2-Bis(4-methoxyphenyl)diselane (4o). A solution of Se-(4methoxybenzyl) N,N-dimethylselenocarbamate (70.5 mg, 259 μmol) in 1.75 M KOH in a degassed (N 2 , 30 min) MeOH/H 2 O mixture [2:1 (v/v), 15 mL] was stirred for 21 h at 25 °C.…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

Benzylic Thio and Seleno Newman–Kwart Rearrangements

et al. 2018

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“…Urea/carbamate-derived phenylpyrazole ROCK inhibitors from SR6442 ( 81 ) to benzyl (4-(1 H -pyrazol-4-yl)phenyl)carbamate ( 85 ) have also been described. ,− Inhibitor 81 is a direct analog of Astellas’ phenylpyridine based ROCK inhibitor 61 (Figure ). However, compound 81 had a much higher ROCK inhibitory potency (IC 50 is 2 nM vs 85 nM for 61 ) due to a 4-ylpyrazole (instead of the pyridine in 61 ) as the hinge binding moiety .…”

Section: Development Of Rock Inhibitors and Their Therapeutic Implica...mentioning

confidence: 99%

“…INS117548 (168), developed by Inspire Pharmaceuticals Inc. (acquired by Merck in 2011), is an isoquinoline derivative 115,266 and a potent inhibitor of ROCK-I and ROCK-II (K i = 5 and 14 nM, respectively). 267 It was shown to be effective at reducing IOP in monkey eyes (20−25% relative to baseline at 1−3 h following instillation).…”

Section: Current Status Of Rock Inhibitorsmentioning

confidence: 99%

Rho Kinase (ROCK) Inhibitors and Their Therapeutic Potential

et al. 2015

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Rho kinases (ROCKs) belong to the serine-threonine family, the inhibition of which affects the function of many downstream substrates. As such, ROCK inhibitors have potential therapeutic applicability in a wide variety of pathological conditions including asthma, cancer, erectile dysfunction, glaucoma, insulin resistance, kidney failure, neuronal degeneration, and osteoporosis. To date, two ROCK inhibitors have been approved for clinical use in Japan (fasudil and ripasudil) and one in China (fasudil). In 1995 fasudil was approved for the treatment of cerebral vasospasm, and more recently, ripasudil was approved for the treatment of glaucoma in 2014. In this Perspective, we present a comprehensive review of the physiological and biological functions for ROCK, the properties and development of over 170 ROCK inhibitors as well as their therapeutic potential, the current status, and future considerations.

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ChemInform Abstract: A Metal‐Free and Recyclable Synthesis of Benzothiazoles Using Thiourea as a Sulfur Surrogate.

et al. 2015

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A Metal-Free and Recyclable Synthesis of Benzothiazoles Using Thiourea as a Sulfur Surrogate. -Treatment of substrates (I) with thiourea and TFA gives benzothiazoles (IV) and TFA salts (V). Furthermore, an analogous two-step sequence allows the synthesis of unsymmetrical disulfides. -(YIN*, Y.; ZHOU, H.; LIU, X.; CHEN, H.; WU, F.; ZHANG, H.; TAO, R.; CHENG, F.; FENG, Y.; Tetrahedron Lett. 56 (2015) 13, 1709-1712, http://dx.

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A metal-free and recyclable synthesis of benzothiazoles using thiourea as a sulfur surrogate

Cited by 4 publications

References 14 publications

Benzylic Thio and Seleno Newman–Kwart Rearrangements

Benzylic Thio and Seleno Newman–Kwart Rearrangements

Rho Kinase (ROCK) Inhibitors and Their Therapeutic Potential

ChemInform Abstract: A Metal‐Free and Recyclable Synthesis of Benzothiazoles Using Thiourea as a Sulfur Surrogate.

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