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Non-bonding 1,5-S···O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles.

Chemical science

Robinson ERT, Walden DM, Fallan C, Greenhalgh MD, Cheong PH, Smith AD.
PMID: 28567263
Chem Sci. 2016 Dec 01;7(12):6919-6927. doi: 10.1039/c6sc00940a. Epub 2016 Jul 04.

Isothiourea-catalyzed annulations between 2-acyl benzazoles and α,β-unsaturated acyl ammonium intermediates are selectively tuned to form either lactam or lactone heterocycles in good yields (up to 95%) and high ee (up to 99%) using benzothiazole or benzoxazole derivatives, respectively. Computation...

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Robinson ERT, Walden DM, Fallan C, et al. Non-bonding 1,5-S···O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles. Chem Sci. 2016;7(12):6919-6927doi: 10.1039/c6sc00940a.
Robinson, E. R. T., Walden, D. M., Fallan, C., Greenhalgh, M. D., Cheong, P. H., & Smith, A. D. (2016). Non-bonding 1,5-S···O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles. Chemical science, 7(12), 6919-6927. https://doi.org/10.1039/c6sc00940a
Robinson, Emily R T, et al. "Non-bonding 1,5-S···O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles." Chemical science vol. 7,12 (2016): 6919-6927. doi: https://doi.org/10.1039/c6sc00940a
Robinson ERT, Walden DM, Fallan C, Greenhalgh MD, Cheong PH, Smith AD. Non-bonding 1,5-S···O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles. Chem Sci. 2016 Dec 01;7(12):6919-6927. doi: 10.1039/c6sc00940a. Epub 2016 Jul 04. PMID: 28567263; PMCID: PMC5450589.
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Identification of non-regulated polycyclic aromatic compounds and other markers of urban pollution in road tunnel particulate matter.

Journal of hazardous materials

Grung M, Kringstad A, Bæk K, Allan IJ, Thomas KV, Meland S, Ranneklev SB.
PMID: 27233209
J Hazard Mater. 2017 Feb 05;323:36-44. doi: 10.1016/j.jhazmat.2016.05.036. Epub 2016 May 12.

A combination of silicone rubber extraction and non-target and suspect screening by gas chromatography coupled to high-resolution time-of flight mass spectrometry was used for the identification of compounds in particulate matter (PM). Tunnel PM is a proxy for local...

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Grung M, Kringstad A, Bæk K, et al. Identification of non-regulated polycyclic aromatic compounds and other markers of urban pollution in road tunnel particulate matter. J Hazard Mater. 2016;323:36-44doi: 10.1016/j.jhazmat.2016.05.036.
Grung, M., Kringstad, A., Bæk, K., Allan, I. J., Thomas, K. V., Meland, S., & Ranneklev, S. B. (2017). Identification of non-regulated polycyclic aromatic compounds and other markers of urban pollution in road tunnel particulate matter. Journal of hazardous materials, 32336-44. https://doi.org/10.1016/j.jhazmat.2016.05.036
Grung, Merete, et al. "Identification of non-regulated polycyclic aromatic compounds and other markers of urban pollution in road tunnel particulate matter." Journal of hazardous materials vol. 323 (2017): 36-44. doi: https://doi.org/10.1016/j.jhazmat.2016.05.036
Grung M, Kringstad A, Bæk K, Allan IJ, Thomas KV, Meland S, Ranneklev SB. Identification of non-regulated polycyclic aromatic compounds and other markers of urban pollution in road tunnel particulate matter. J Hazard Mater. 2017 Feb 05;323:36-44. doi: 10.1016/j.jhazmat.2016.05.036. Epub 2016 May 12. PMID: 27233209.
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Intramolecular Rearrangement of α-Amino Acid Amide Derivatives of 2-Aminobenzothiazoles.

Tetrahedron letters

Pelletier JC, Velvadapu V, McDonnell ME, Wrobel JE, Reitz AB.
PMID: 25018567
Tetrahedron Lett. 2014 Jul 23;55(30):4193-4195. doi: 10.1016/j.tetlet.2014.05.046.

We have found that α-amino acid amide derivatives of 2-aminobenzothiazoles undergo a time-dependent, thermal rearrangement in which the amine group attacks the 2-position carbon of the thiazole ring to form a 5,5-spiro ring system. This is followed by sulfur...

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Pelletier JC, Velvadapu V, McDonnell ME, et al. Intramolecular Rearrangement of α-Amino Acid Amide Derivatives of 2-Aminobenzothiazoles. Tetrahedron Lett. 2014;55(30):4193-4195doi: 10.1016/j.tetlet.2014.05.046.
Pelletier, J. C., Velvadapu, V., McDonnell, M. E., Wrobel, J. E., & Reitz, A. B. (2014). Intramolecular Rearrangement of α-Amino Acid Amide Derivatives of 2-Aminobenzothiazoles. Tetrahedron letters, 55(30), 4193-4195. https://doi.org/10.1016/j.tetlet.2014.05.046
Pelletier, Jeffrey C, et al. "Intramolecular Rearrangement of α-Amino Acid Amide Derivatives of 2-Aminobenzothiazoles." Tetrahedron letters vol. 55,30 (2014): 4193-4195. doi: https://doi.org/10.1016/j.tetlet.2014.05.046
Pelletier JC, Velvadapu V, McDonnell ME, Wrobel JE, Reitz AB. Intramolecular Rearrangement of α-Amino Acid Amide Derivatives of 2-Aminobenzothiazoles. Tetrahedron Lett. 2014 Jul 23;55(30):4193-4195. doi: 10.1016/j.tetlet.2014.05.046. PMID: 25018567; PMCID: PMC4090782.
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Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles.

Organic letters

Wang J, Li J, Zhu Q.
PMID: 26509678
Org Lett. 2015 Nov 06;17(21):5336-9. doi: 10.1021/acs.orglett.5b02694. Epub 2015 Oct 28.

A tunable route to both isomers of benzo[d]imidazothiazole has been developed through copper-promoted cycloaddition of α-methylenyl isocyanides with benzothiazoles. When the C2 position of benzothiazole is linked to a C-H or C-C bond, benzo[d]imidazo[2,1-b]thiazoles are obtained through a novel...

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Wang J, Li J, Zhu Q. Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles. Org Lett. 2015;17(21):5336-9doi: 10.1021/acs.orglett.5b02694.
Wang, J., Li, J., & Zhu, Q. (2015). Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles. Organic letters, 17(21), 5336-9. https://doi.org/10.1021/acs.orglett.5b02694
Wang, Jian, et al. "Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles." Organic letters vol. 17,21 (2015): 5336-9. doi: https://doi.org/10.1021/acs.orglett.5b02694
Wang J, Li J, Zhu Q. Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles. Org Lett. 2015 Nov 06;17(21):5336-9. doi: 10.1021/acs.orglett.5b02694. Epub 2015 Oct 28. PMID: 26509678.
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A new three-carbon synthon for efficient synthesis of benzannelated and 1-(2-arylethenyl) heterocycles.

The Journal of organic chemistry

Katritzky AR, Tymoshenko DO, Monteux D, Vvedensky V, Nikonov G, Cooper CB, Deshpande M.
PMID: 11073617
J Org Chem. 2000 Nov 17;65(23):8059-62. doi: 10.1021/jo000946r.

The novel three-carbon synthon 1-(1H-1,2, 3-benzotriazol-1-yl)-3-chloroacetone for the synthesis of benzothiazoles, pyrido[1,2-a]indoles, and styryl-substituted indolizines and imidazo[1,2-a]pyridines is reported. The proposed routes are a general and efficient approach for heterocyclizations followed by benzannelations or attachment of arylethenyl pharmacophores.

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Katritzky AR, Tymoshenko DO, Monteux D, et al. A new three-carbon synthon for efficient synthesis of benzannelated and 1-(2-arylethenyl) heterocycles. J Org Chem. 2000;65(23):8059-62doi: 10.1021/jo000946r.
Katritzky, A. R., Tymoshenko, D. O., Monteux, D., Vvedensky, V., Nikonov, G., Cooper, C. B., & Deshpande, M. (2000). A new three-carbon synthon for efficient synthesis of benzannelated and 1-(2-arylethenyl) heterocycles. The Journal of organic chemistry, 65(23), 8059-62. https://doi.org/10.1021/jo000946r
Katritzky, et al. "A new three-carbon synthon for efficient synthesis of benzannelated and 1-(2-arylethenyl) heterocycles." The Journal of organic chemistry vol. 65,23 (2000): 8059-62. doi: https://doi.org/10.1021/jo000946r
Katritzky AR, Tymoshenko DO, Monteux D, Vvedensky V, Nikonov G, Cooper CB, Deshpande M. A new three-carbon synthon for efficient synthesis of benzannelated and 1-(2-arylethenyl) heterocycles. J Org Chem. 2000 Nov 17;65(23):8059-62. doi: 10.1021/jo000946r. PMID: 11073617.
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Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-methoxy-TEMPO.

Angewandte Chemie (International ed. in English)

Chen YX, Qian LF, Zhang W, Han B.
PMID: 18972469
Angew Chem Int Ed Engl. 2008;47(48):9330-3. doi: 10.1002/anie.200803381.

No abstract available.

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Chen YX, Qian LF, Zhang W, et al. Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-methoxy-TEMPO. Angew Chem Int Ed Engl. 2008;47(48):9330-3doi: 10.1002/anie.200803381.
Chen, Y. X., Qian, L. F., Zhang, W., & Han, B. (2008). Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-methoxy-TEMPO. Angewandte Chemie (International ed. in English), 47(48), 9330-3. https://doi.org/10.1002/anie.200803381
Chen, Yong-Xing, et al. "Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-methoxy-TEMPO." Angewandte Chemie (International ed. in English) vol. 47,48 (2008): 9330-3. doi: https://doi.org/10.1002/anie.200803381
Chen YX, Qian LF, Zhang W, Han B. Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-methoxy-TEMPO. Angew Chem Int Ed Engl. 2008;47(48):9330-3. doi: 10.1002/anie.200803381. PMID: 18972469.
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Determination of benzotriazole corrosion inhibitors from aqueous environmental samples by liquid chromatography-electrospray ionization-tandem mass spectrometry.

Analytical chemistry

Weiss S, Reemtsma T.
PMID: 16285694
Anal Chem. 2005 Nov 15;77(22):7415-20. doi: 10.1021/ac051203e.

The first method for the determination of commonly used corrosion inhibitors in environmental water samples by liquid chromatography-electrospray ionization-tandem mass spectrometry is presented. Benzotriazole (BTri) and the two isomers of tolyltriazole (5- and 4-TTri) are separated in an isocratic...

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Weiss S, Reemtsma T. Determination of benzotriazole corrosion inhibitors from aqueous environmental samples by liquid chromatography-electrospray ionization-tandem mass spectrometry. Anal Chem. 2005;77(22):7415-20doi: 10.1021/ac051203e.
Weiss, S., & Reemtsma, T. (2005). Determination of benzotriazole corrosion inhibitors from aqueous environmental samples by liquid chromatography-electrospray ionization-tandem mass spectrometry. Analytical chemistry, 77(22), 7415-20. https://doi.org/10.1021/ac051203e
Weiss, Stefan, and Reemtsma, Thorsten. "Determination of benzotriazole corrosion inhibitors from aqueous environmental samples by liquid chromatography-electrospray ionization-tandem mass spectrometry." Analytical chemistry vol. 77,22 (2005): 7415-20. doi: https://doi.org/10.1021/ac051203e
Weiss S, Reemtsma T. Determination of benzotriazole corrosion inhibitors from aqueous environmental samples by liquid chromatography-electrospray ionization-tandem mass spectrometry. Anal Chem. 2005 Nov 15;77(22):7415-20. doi: 10.1021/ac051203e. PMID: 16285694.
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Synthesis, Characterization, and Biological Evaluation of certain 6-methyl-2(3H)-benzo-1, 3-thiazolyl-1'-ethylidene-2-(o, p- Substituted Acetophenones) Hydrazine Analogs.

Journal of young pharmacists : JYP

Alang G, Kaur G, Kaur R, Singh A, Tiwari R.
PMID: 21264101
J Young Pharm. 2010 Oct;2(4):394-8. doi: 10.4103/0975-1483.71636.

In the present study, five new derivatives (GG4 to GG8) of benzothiazoles were synthesized and evaluated against Staphylococcus aureus (MTCC 737), Pseudomonas aeruginosa (MTCC 424), Escherichia coli (MTCC 1687), and yeast-like fungi Candida tropicalis. p-Toluidine on treatment with ammonium...

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Alang G, Kaur G, Kaur R, et al. Synthesis, Characterization, and Biological Evaluation of certain 6-methyl-2(3H)-benzo-1, 3-thiazolyl-1'-ethylidene-2-(o, p- Substituted Acetophenones) Hydrazine Analogs. J Young Pharm. 2010;2(4):394-8doi: 10.4103/0975-1483.71636.
Alang, G., Kaur, G., Kaur, R., Singh, A., & Tiwari, R. (2010). Synthesis, Characterization, and Biological Evaluation of certain 6-methyl-2(3H)-benzo-1, 3-thiazolyl-1'-ethylidene-2-(o, p- Substituted Acetophenones) Hydrazine Analogs. Journal of young pharmacists : JYP, 2(4), 394-8. https://doi.org/10.4103/0975-1483.71636
Alang, G, et al. "Synthesis, Characterization, and Biological Evaluation of certain 6-methyl-2(3H)-benzo-1, 3-thiazolyl-1'-ethylidene-2-(o, p- Substituted Acetophenones) Hydrazine Analogs." Journal of young pharmacists : JYP vol. 2,4 (2010): 394-8. doi: https://doi.org/10.4103/0975-1483.71636
Alang G, Kaur G, Kaur R, Singh A, Tiwari R. Synthesis, Characterization, and Biological Evaluation of certain 6-methyl-2(3H)-benzo-1, 3-thiazolyl-1'-ethylidene-2-(o, p- Substituted Acetophenones) Hydrazine Analogs. J Young Pharm. 2010 Oct;2(4):394-8. doi: 10.4103/0975-1483.71636. PMID: 21264101; PMCID: PMC3019380.
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Microbial transformations and biological effects of fungicide-derived benzothiazoles determined in industrial wastewater.

Environmental science & technology

Reemtsma T, Fiehn O, Kalnowski G, Jekel M.
PMID: 22201395
Environ Sci Technol. 1995 Feb 01;29(2):478-85. doi: 10.1021/es00002a025.

No abstract available.

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Reemtsma T, Fiehn O, Kalnowski G, et al. Microbial transformations and biological effects of fungicide-derived benzothiazoles determined in industrial wastewater. Environ Sci Technol. 1995;29(2):478-85doi: 10.1021/es00002a025.
Reemtsma, T., Fiehn, O., Kalnowski, G., & Jekel, M. (1995). Microbial transformations and biological effects of fungicide-derived benzothiazoles determined in industrial wastewater. Environmental science & technology, 29(2), 478-85. https://doi.org/10.1021/es00002a025
Reemtsma, T, et al. "Microbial transformations and biological effects of fungicide-derived benzothiazoles determined in industrial wastewater." Environmental science & technology vol. 29,2 (1995): 478-85. doi: https://doi.org/10.1021/es00002a025
Reemtsma T, Fiehn O, Kalnowski G, Jekel M. Microbial transformations and biological effects of fungicide-derived benzothiazoles determined in industrial wastewater. Environ Sci Technol. 1995 Feb 01;29(2):478-85. doi: 10.1021/es00002a025. PMID: 22201395.
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TBHP-mediated oxidative thiolation of an sp3 C-H bond adjacent to a nitrogen atom in an amide.

Chemical communications (Cambridge, England)

Tang RY, Xie YX, Xie YL, Xiang JN, Li JH.
PMID: 22037478
Chem Commun (Camb). 2011 Dec 28;47(48):12867-9. doi: 10.1039/c1cc15397h. Epub 2011 Oct 31.

The first example of molecular sieve-promoted TBHP-mediated direct oxidative thiolation of an sp(3) C-H bond adjacent to a nitrogen atom with disulfides under metal-free conditions, which allows for preparation of numerous S,N-containing compounds, is presented. Moreover, diverse benzothiazoles and...

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Tang RY, Xie YX, Xie YL, et al. TBHP-mediated oxidative thiolation of an sp3 C-H bond adjacent to a nitrogen atom in an amide. Chem Commun (Camb). 2011;47(48):12867-9doi: 10.1039/c1cc15397h.
Tang, R. Y., Xie, Y. X., Xie, Y. L., Xiang, J. N., & Li, J. H. (2011). TBHP-mediated oxidative thiolation of an sp3 C-H bond adjacent to a nitrogen atom in an amide. Chemical communications (Cambridge, England), 47(48), 12867-9. https://doi.org/10.1039/c1cc15397h
Tang, Ri-Yuan, et al. "TBHP-mediated oxidative thiolation of an sp3 C-H bond adjacent to a nitrogen atom in an amide." Chemical communications (Cambridge, England) vol. 47,48 (2011): 12867-9. doi: https://doi.org/10.1039/c1cc15397h
Tang RY, Xie YX, Xie YL, Xiang JN, Li JH. TBHP-mediated oxidative thiolation of an sp3 C-H bond adjacent to a nitrogen atom in an amide. Chem Commun (Camb). 2011 Dec 28;47(48):12867-9. doi: 10.1039/c1cc15397h. Epub 2011 Oct 31. PMID: 22037478.
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Metal-free cascade intramolecular S-arylation: regioselective synthesis of substituted benzothiazoles.

The Journal of organic chemistry

[No authors listed]
PMID: 21902272
J Org Chem. 2011 Sep 16;76(18):7630. doi: 10.1021/jo802826x. Epub 2009 Feb 11.

No abstract available.

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Metal-free cascade intramolecular S-arylation: regioselective synthesis of substituted benzothiazoles. J Org Chem. 2009;76(18):7630doi: 10.1021/jo802826x.
(2011). Metal-free cascade intramolecular S-arylation: regioselective synthesis of substituted benzothiazoles. The Journal of organic chemistry, 76(18), 7630. https://doi.org/10.1021/jo802826x
"Metal-free cascade intramolecular S-arylation: regioselective synthesis of substituted benzothiazoles." The Journal of organic chemistry vol. 76,18 (2011): 7630. doi: https://doi.org/10.1021/jo802826x
Metal-free cascade intramolecular S-arylation: regioselective synthesis of substituted benzothiazoles. J Org Chem. 2011 Sep 16;76(18):7630. doi: 10.1021/jo802826x. Epub 2009 Feb 11. PMID: 21902272.
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The role of aryl hydrocarbon receptor and crosstalk with estrogen receptor in response of breast cancer cells to the novel antitumor agents benzothiazoles and aminoflavone.

International journal of breast cancer

Callero MA, Loaiza-Pérez AI.
PMID: 22295239
Int J Breast Cancer. 2011;2011:923250. doi: 10.4061/2011/923250. Epub 2011 Sep 22.

Many estrogen-receptor- (ER-) expressing breast cancers become refractory to ER-based therapies. New antitumor drugs like aminoflavone (AF) and benzothiazoles (Bzs) have been developed and have exquisite antitumor activity in ER+MCF-7 and T47D cells and in a MCF-7 nude mouse...

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Callero MA, Loaiza-Pérez AI. The role of aryl hydrocarbon receptor and crosstalk with estrogen receptor in response of breast cancer cells to the novel antitumor agents benzothiazoles and aminoflavone. Int J Breast Cancer. 2011;2011:923250doi: 10.4061/2011/923250.
Callero, M. A., & Loaiza-Pérez, A. I. (2011). The role of aryl hydrocarbon receptor and crosstalk with estrogen receptor in response of breast cancer cells to the novel antitumor agents benzothiazoles and aminoflavone. International journal of breast cancer, 2011923250. https://doi.org/10.4061/2011/923250
Callero, Mariana A, and Loaiza-Pérez, Andrea I. "The role of aryl hydrocarbon receptor and crosstalk with estrogen receptor in response of breast cancer cells to the novel antitumor agents benzothiazoles and aminoflavone." International journal of breast cancer vol. 2011 (2011): 923250. doi: https://doi.org/10.4061/2011/923250
Callero MA, Loaiza-Pérez AI. The role of aryl hydrocarbon receptor and crosstalk with estrogen receptor in response of breast cancer cells to the novel antitumor agents benzothiazoles and aminoflavone. Int J Breast Cancer. 2011;2011:923250. doi: 10.4061/2011/923250. Epub 2011 Sep 22. PMID: 22295239; PMCID: PMC3262585.
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Showing 1 to 12 of 153 entries