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Synthesis of Brominated Thiazoles via Sequential Bromination-Debromination Methods.

The Journal of organic chemistry

Uzelac EJ, Rasmussen SC.
PMID: 28508637
J Org Chem. 2017 Jun 02;82(11):5947-5951. doi: 10.1021/acs.joc.7b00495. Epub 2017 May 16.

The synthesis of the full family of bromothiazoles has been revisited in order to update and optimize their production. The species reported include 2-bromothiazole, 4-bromothiazole, 5-bromothiazole, 2,4-dibromothiazole, 2,5-dibromothiazole, 4,5-dibromothiazole, and 2,4,5-tribromothiazole, the majority of which are produced via sequential...

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Uzelac EJ, Rasmussen SC. Synthesis of Brominated Thiazoles via Sequential Bromination-Debromination Methods. J Org Chem. 2017;82(11):5947-5951doi: 10.1021/acs.joc.7b00495.
Uzelac, E. J., & Rasmussen, S. C. (2017). Synthesis of Brominated Thiazoles via Sequential Bromination-Debromination Methods. The Journal of organic chemistry, 82(11), 5947-5951. https://doi.org/10.1021/acs.joc.7b00495
Uzelac, Eric J, and Rasmussen, Seth C. "Synthesis of Brominated Thiazoles via Sequential Bromination-Debromination Methods." The Journal of organic chemistry vol. 82,11 (2017): 5947-5951. doi: https://doi.org/10.1021/acs.joc.7b00495
Uzelac EJ, Rasmussen SC. Synthesis of Brominated Thiazoles via Sequential Bromination-Debromination Methods. J Org Chem. 2017 Jun 02;82(11):5947-5951. doi: 10.1021/acs.joc.7b00495. Epub 2017 May 16. PMID: 28508637.
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Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles.

Organic & biomolecular chemistry

Shen GL, Sun J, Yan CG.
PMID: 26373777
Org Biomol Chem. 2015 Nov 28;13(44):10929-38. doi: 10.1039/c5ob01374g. Epub 2015 Sep 16.

The domino cycloaddition reactions of N-phenacylbenzothiazolium bromides with 3-phenacylideneoxindoles or ethyl 2-(2-oxoindolin-3-ylidene)acetates in ethanol at room temperature in the presence of triethylamine as a base afforded functionalized spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] in good yields and with high diastereoselectivity. The similar reactions of...

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Shen GL, Sun J, Yan CG. Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles. Org Biomol Chem. 2015;13(44):10929-38doi: 10.1039/c5ob01374g.
Shen, G. L., Sun, J., & Yan, C. G. (2015). Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles. Organic & biomolecular chemistry, 13(44), 10929-38. https://doi.org/10.1039/c5ob01374g
Shen, Guo-Liang, et al. "Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles." Organic & biomolecular chemistry vol. 13,44 (2015): 10929-38. doi: https://doi.org/10.1039/c5ob01374g
Shen GL, Sun J, Yan CG. Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles. Org Biomol Chem. 2015 Nov 28;13(44):10929-38. doi: 10.1039/c5ob01374g. Epub 2015 Sep 16. PMID: 26373777.
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Microwave-assisted one pot three-component synthesis of some novel pyrazole scaffolds as potent anticancer agents.

Chemistry Central journal

Gomha SM, Edrees MM, Faty RAM, Muhammad ZA, Mabkhot YN.
PMID: 29086808
Chem Cent J. 2017 May 08;11(1):37. doi: 10.1186/s13065-017-0266-4.

BACKGROUND: Pyrazoles, thiazoles and 1,3,4-thiadiazoles have been reported to possess various pharmacological activities.RESULTS: An efficient and a novel approach for the synthesis of some novel pyrazole based-azoles are described via multi-component reaction under controlled microwave heating conditions. The structures...

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Gomha SM, Edrees MM, Faty RAM, et al. Microwave-assisted one pot three-component synthesis of some novel pyrazole scaffolds as potent anticancer agents. Chem Cent J. 2017;11(1):37doi: 10.1186/s13065-017-0266-4.
Gomha, S. M., Edrees, M. M., Faty, R. A. M., Muhammad, Z. A., & Mabkhot, Y. N. (2017). Microwave-assisted one pot three-component synthesis of some novel pyrazole scaffolds as potent anticancer agents. Chemistry Central journal, 11(1), 37. https://doi.org/10.1186/s13065-017-0266-4
Gomha, Sobhi M, et al. "Microwave-assisted one pot three-component synthesis of some novel pyrazole scaffolds as potent anticancer agents." Chemistry Central journal vol. 11,1 (2017): 37. doi: https://doi.org/10.1186/s13065-017-0266-4
Gomha SM, Edrees MM, Faty RAM, Muhammad ZA, Mabkhot YN. Microwave-assisted one pot three-component synthesis of some novel pyrazole scaffolds as potent anticancer agents. Chem Cent J. 2017 May 08;11(1):37. doi: 10.1186/s13065-017-0266-4. PMID: 29086808; PMCID: PMC5422217.
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Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles.

The Journal of organic chemistry

Zhang J, Lu X, Li T, Wang S, Zhong G.
PMID: 28429945
J Org Chem. 2017 May 19;82(10):5222-5229. doi: 10.1021/acs.joc.7b00480. Epub 2017 Apr 27.

A catalytic oxidative cyclization of 2-aminopyridines or 2-aminobenzothiazole with 2-phenoxyacetophenones (a kind of lignin platform compound) was developed, efficiently providing valuable 3-phenoxy imidazo[1,2-a]pyridines or 3-phenoxy benzo[d]imidazo[2,1-b]thiazoles. The reaction was realized under oxygen by simply using inexpensive CuI as the...

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Zhang J, Lu X, Li T, et al. Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles. J Org Chem. 2017;82(10):5222-5229doi: 10.1021/acs.joc.7b00480.
Zhang, J., Lu, X., Li, T., Wang, S., & Zhong, G. (2017). Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles. The Journal of organic chemistry, 82(10), 5222-5229. https://doi.org/10.1021/acs.joc.7b00480
Zhang, Jian, et al. "Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles." The Journal of organic chemistry vol. 82,10 (2017): 5222-5229. doi: https://doi.org/10.1021/acs.joc.7b00480
Zhang J, Lu X, Li T, Wang S, Zhong G. Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles. J Org Chem. 2017 May 19;82(10):5222-5229. doi: 10.1021/acs.joc.7b00480. Epub 2017 Apr 27. PMID: 28429945.
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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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Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate.

Organic & biomolecular chemistry

Chen XB, Wang XQ, Song JN, Yang QL, Huang C, Liu W.
PMID: 28401235
Org Biomol Chem. 2017 May 03;15(17):3611-3615. doi: 10.1039/c7ob00306d.

A novel and highly efficient protocol has been developed for the regioselective synthesis of 2-iminothiazole derivatives with potential biochemical interest by the reaction of enaminones, potassium thiocyanate (KSCN), and N-bromo succinimide (NBS) under mild conditions. The reaction proceeds via...

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Chen XB, Wang XQ, Song JN, et al. Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate. Org Biomol Chem. 2017;15(17):3611-3615doi: 10.1039/c7ob00306d.
Chen, X. B., Wang, X. Q., Song, J. N., Yang, Q. L., Huang, C., & Liu, W. (2017). Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate. Organic & biomolecular chemistry, 15(17), 3611-3615. https://doi.org/10.1039/c7ob00306d
Chen, Xue-Bing, et al. "Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate." Organic & biomolecular chemistry vol. 15,17 (2017): 3611-3615. doi: https://doi.org/10.1039/c7ob00306d
Chen XB, Wang XQ, Song JN, Yang QL, Huang C, Liu W. Efficient construction of C-N and C-S bonds in 2-iminothiazoles via cascade reaction of enaminones with potassium thiocyanate. Org Biomol Chem. 2017 May 03;15(17):3611-3615. doi: 10.1039/c7ob00306d. PMID: 28401235.
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Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles.

The Journal of organic chemistry

Rasheed S, Rao DN, Das P.
PMID: 26322501
J Org Chem. 2015 Sep 18;80(18):9321-7. doi: 10.1021/acs.joc.5b01396. Epub 2015 Sep 08.

A Cu (II)-catalyzed, inter/intramolecular C-N bond formation for the synthesis of various benzimidazole-fused heterocycles in a concise manner has been reported. The robustness of this reaction is demonstrated by the synthesis of a series of benzimidazole-fused heteroaromatics (e.g., pyrido[1,2-a]...

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Rasheed S, Rao DN, Das P. Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles. J Org Chem. 2015;80(18):9321-7doi: 10.1021/acs.joc.5b01396.
Rasheed, S., Rao, D. N., & Das, P. (2015). Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles. The Journal of organic chemistry, 80(18), 9321-7. https://doi.org/10.1021/acs.joc.5b01396
Rasheed, Sk, et al. "Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles." The Journal of organic chemistry vol. 80,18 (2015): 9321-7. doi: https://doi.org/10.1021/acs.joc.5b01396
Rasheed S, Rao DN, Das P. Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles. J Org Chem. 2015 Sep 18;80(18):9321-7. doi: 10.1021/acs.joc.5b01396. Epub 2015 Sep 08. PMID: 26322501.
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Synthesis and antimicrobial evaluation of certain novel thiazoles.

Advanced pharmaceutical bulletin

Sreedevi M, Guru Prasad AR, Spoorthy YN, Ravindranath LR.
PMID: 24312840
Adv Pharm Bull. 2013;3(1):227-30. doi: 10.5681/apb.2013.037. Epub 2013 Feb 07.

PURPOSE: This article makes an attempt to synthesize certain compounds containing thiazole and imidazole moieties and screen for the antimicrobial properties.METHODS: The novel compounds synthesized were characterized by elemental analysis, IR and (1)HNMR spectral data. The antimicrobial activity of...

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Sreedevi M, Guru Prasad AR, Spoorthy YN, et al. Synthesis and antimicrobial evaluation of certain novel thiazoles. Adv Pharm Bull. 2013;3(1):227-30doi: 10.5681/apb.2013.037.
Sreedevi, M., Guru Prasad, A. R., Spoorthy, Y. N., & Ravindranath, L. R. (2013). Synthesis and antimicrobial evaluation of certain novel thiazoles. Advanced pharmaceutical bulletin, 3(1), 227-30. https://doi.org/10.5681/apb.2013.037
Sreedevi, Meesaraganda, et al. "Synthesis and antimicrobial evaluation of certain novel thiazoles." Advanced pharmaceutical bulletin vol. 3,1 (2013): 227-30. doi: https://doi.org/10.5681/apb.2013.037
Sreedevi M, Guru Prasad AR, Spoorthy YN, Ravindranath LR. Synthesis and antimicrobial evaluation of certain novel thiazoles. Adv Pharm Bull. 2013;3(1):227-30. doi: 10.5681/apb.2013.037. Epub 2013 Feb 07. PMID: 24312840; PMCID: PMC3846066.
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Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines.

Organic & biomolecular chemistry

Samanta S, Jana S, Mondal S, Monir K, Chandra SK, Hajra A.
PMID: 27182027
Org Biomol Chem. 2016 Jun 14;14(22):5073-8. doi: 10.1039/c6ob00656f. Epub 2016 May 16.

A unique copper-catalyzed binucleophilic switching of 2-aminopyridine has been developed for the regioselective synthesis of 2- and 3-iodoimidazo[1,2-a]pyridines using alkenes/alkynes as coupling partners in the presence of molecular iodine under aerobic reaction conditions. This method was also applied to...

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Samanta S, Jana S, Mondal S, et al. Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines. Org Biomol Chem. 2016;14(22):5073-8doi: 10.1039/c6ob00656f.
Samanta, S., Jana, S., Mondal, S., Monir, K., Chandra, S. K., & Hajra, A. (2016). Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines. Organic & biomolecular chemistry, 14(22), 5073-8. https://doi.org/10.1039/c6ob00656f
Samanta, Sadhanendu, et al. "Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines." Organic & biomolecular chemistry vol. 14,22 (2016): 5073-8. doi: https://doi.org/10.1039/c6ob00656f
Samanta S, Jana S, Mondal S, Monir K, Chandra SK, Hajra A. Switching the regioselectivity in the copper-catalyzed synthesis of iodoimidazo[1,2-a]pyridines. Org Biomol Chem. 2016 Jun 14;14(22):5073-8. doi: 10.1039/c6ob00656f. Epub 2016 May 16. PMID: 27182027.
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Nonracemic 2-diazo-1-oxiranyl-ethanone, a versatile chiral epoxide educt in diazocarbonyl reactions.

Organic letters

Groarke M, McKervey MA, Miel H, Nieuwenhuyzen M.
PMID: 10956504
Org Lett. 2000 Aug 10;2(16):2393-5. doi: 10.1021/ol000034b.

(S)-(-)-2-Diazo-1-oxiranyl-ethanone, prepared in two steps from (R)-(+)-glycidol, has been employed as an intermediate in several characteristic diazocarbonyl reactions to yield novel, nonracemic products including an epoxy quinoxaline and epoxy thiazoles and oxazoles.

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Groarke M, McKervey MA, Miel H, et al. Nonracemic 2-diazo-1-oxiranyl-ethanone, a versatile chiral epoxide educt in diazocarbonyl reactions. Org Lett. 2000;2(16):2393-5doi: 10.1021/ol000034b.
Groarke, M., McKervey, M. A., Miel, H., & Nieuwenhuyzen, M. (2000). Nonracemic 2-diazo-1-oxiranyl-ethanone, a versatile chiral epoxide educt in diazocarbonyl reactions. Organic letters, 2(16), 2393-5. https://doi.org/10.1021/ol000034b
Groarke, et al. "Nonracemic 2-diazo-1-oxiranyl-ethanone, a versatile chiral epoxide educt in diazocarbonyl reactions." Organic letters vol. 2,16 (2000): 2393-5. doi: https://doi.org/10.1021/ol000034b
Groarke M, McKervey MA, Miel H, Nieuwenhuyzen M. Nonracemic 2-diazo-1-oxiranyl-ethanone, a versatile chiral epoxide educt in diazocarbonyl reactions. Org Lett. 2000 Aug 10;2(16):2393-5. doi: 10.1021/ol000034b. PMID: 10956504.
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Synthesis of an Enantiomerically Pure Serine-Derived Thiazole.

The Journal of organic chemistry

Sowinski JA, Toogood PL.
PMID: 11667720
J Org Chem. 1996 Nov 01;61(22):7671-7676. doi: 10.1021/jo961408a.

Previously reported methods for preparing enantiomerically pure thiazoles are inadequate for the synthesis of inherently labile O-alkyl serine-derived thiazoles. The intermediateN-Boc-(O-methylseryl) thiazolines are very susceptible to tautomerization, even under neutral conditions (Scheme 5). Herein, it is demonstrated that the...

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Sowinski JA, Toogood PL. Synthesis of an Enantiomerically Pure Serine-Derived Thiazole. J Org Chem. 1996;61(22):7671-7676doi: 10.1021/jo961408a.
Sowinski, J. A., & Toogood, P. L. (1996). Synthesis of an Enantiomerically Pure Serine-Derived Thiazole. The Journal of organic chemistry, 61(22), 7671-7676. https://doi.org/10.1021/jo961408a
Sowinski, Jennifer A., and Toogood, Peter L.. "Synthesis of an Enantiomerically Pure Serine-Derived Thiazole." The Journal of organic chemistry vol. 61,22 (1996): 7671-7676. doi: https://doi.org/10.1021/jo961408a
Sowinski JA, Toogood PL. Synthesis of an Enantiomerically Pure Serine-Derived Thiazole. J Org Chem. 1996 Nov 01;61(22):7671-7676. doi: 10.1021/jo961408a. PMID: 11667720.
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Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch-Sosnovsky Reaction.

The Journal of organic chemistry

Meyers AI, Tavares FX.
PMID: 11667808
J Org Chem. 1996 Nov 15;61(23):8207-8215. doi: 10.1021/jo9613491.

Using a modification of the Kharasch-Sosnovsky reaction, the oxidation of oxazolines and thiazolines bearing a variety of 2-alkyl substituents (chiral and achiral) were smoothly oxidized to their corresponding oxazoles and thiazoles, respectively. The key feature involved in the successful...

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Meyers AI, Tavares FX. Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch-Sosnovsky Reaction. J Org Chem. 1996;61(23):8207-8215doi: 10.1021/jo9613491.
Meyers, A. I., & Tavares, F. X. (1996). Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch-Sosnovsky Reaction. The Journal of organic chemistry, 61(23), 8207-8215. https://doi.org/10.1021/jo9613491
Meyers, A. I., and Tavares, Francis X.. "Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch-Sosnovsky Reaction." The Journal of organic chemistry vol. 61,23 (1996): 8207-8215. doi: https://doi.org/10.1021/jo9613491
Meyers AI, Tavares FX. Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch-Sosnovsky Reaction. J Org Chem. 1996 Nov 15;61(23):8207-8215. doi: 10.1021/jo9613491. PMID: 11667808.
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Showing 1 to 12 of 198 entries