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Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials.

Angewandte Chemie (International ed. in English)

Li B, Lan J, Wu D, You J.
PMID: 26403373
Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14008-12. doi: 10.1002/anie.201507272. Epub 2015 Sep 25.

Reported herein is the first example of a transition-metal-catalyzed internal oxidative C-H/C-H cross-coupling between two (hetero)arenes through a traceless oxidation directing strategy. Without the requirement of an external metal oxidant, a wide range of phenols, including phenol-containing natural products,...

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Li B, Lan J, Wu D, et al. Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials. Angew Chem Int Ed Engl. 2015;54(47):14008-12doi: 10.1002/anie.201507272.
Li, B., Lan, J., Wu, D., & You, J. (2015). Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials. Angewandte Chemie (International ed. in English), 54(47), 14008-12. https://doi.org/10.1002/anie.201507272
Li, Bijin, et al. "Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials." Angewandte Chemie (International ed. in English) vol. 54,47 (2015): 14008-12. doi: https://doi.org/10.1002/anie.201507272
Li B, Lan J, Wu D, You J. Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative C-H Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials. Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14008-12. doi: 10.1002/anie.201507272. Epub 2015 Sep 25. PMID: 26403373.
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Azlactone Reaction Developments.

Chemistry (Weinheim an der Bergstrasse, Germany)

de Castro PP, Carpanez AG, Amarante GW.
PMID: 27245128
Chemistry. 2016 Jul 18;22(30):10294-318. doi: 10.1002/chem.201600071. Epub 2016 Jun 01.

Azlactones (also known as oxazolones) are heterocycles usually employed in the stereoselective synthesis of α,α-amino acids, heterocycles and natural products. The versatility of the azlactone scaffold arises from the numerous reactive sites, allowing its application in a diversity of...

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de Castro PP, Carpanez AG, Amarante GW. Azlactone Reaction Developments. Chemistry. 2016;22(30):10294-318doi: 10.1002/chem.201600071.
de Castro, P. P., Carpanez, A. G., & Amarante, G. W. (2016). Azlactone Reaction Developments. Chemistry (Weinheim an der Bergstrasse, Germany), 22(30), 10294-318. https://doi.org/10.1002/chem.201600071
de Castro, Pedro P, et al. "Azlactone Reaction Developments." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,30 (2016): 10294-318. doi: https://doi.org/10.1002/chem.201600071
de Castro PP, Carpanez AG, Amarante GW. Azlactone Reaction Developments. Chemistry. 2016 Jul 18;22(30):10294-318. doi: 10.1002/chem.201600071. Epub 2016 Jun 01. PMID: 27245128.
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Oxazoles for click chemistry II: synthesis of extended heterocyclic scaffolds.

Tetrahedron letters

Patil PC, Luzzio FA, Demuth DR.
PMID: 26120210
Tetrahedron Lett. 2015 Jun 03;56(23):3039-3041. doi: 10.1016/j.tetlet.2014.11.014.

New routes to 2, 4, 5-trisubstituted oxazoles were established whereby the substitution pattern was established by the structure of the starting nonsymmetrical acyloins. 2-Chloromethyl-4, 5-disubstituted oxazoles were prepared by refinements of an earlier described process whereby chloroacetyl esters of...

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Patil PC, Luzzio FA, Demuth DR. Oxazoles for click chemistry II: synthesis of extended heterocyclic scaffolds. Tetrahedron Lett. 2015;56(23):3039-3041doi: 10.1016/j.tetlet.2014.11.014.
Patil, P. C., Luzzio, F. A., & Demuth, D. R. (2015). Oxazoles for click chemistry II: synthesis of extended heterocyclic scaffolds. Tetrahedron letters, 56(23), 3039-3041. https://doi.org/10.1016/j.tetlet.2014.11.014
Patil, Pravin C, et al. "Oxazoles for click chemistry II: synthesis of extended heterocyclic scaffolds." Tetrahedron letters vol. 56,23 (2015): 3039-3041. doi: https://doi.org/10.1016/j.tetlet.2014.11.014
Patil PC, Luzzio FA, Demuth DR. Oxazoles for click chemistry II: synthesis of extended heterocyclic scaffolds. Tetrahedron Lett. 2015 Jun 03;56(23):3039-3041. doi: 10.1016/j.tetlet.2014.11.014. PMID: 26120210; PMCID: PMC4480780.
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Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent Postphotochemical Multicomponent Modifications.

Organic letters

Kumar NN, Kutateladze AG.
PMID: 26760049
Org Lett. 2016 Feb 05;18(3):460-3. doi: 10.1021/acs.orglett.5b03503. Epub 2016 Jan 13.

Photogenerated aza-o-xylylenes undergo intramolecular cycloaddition reactions to tethered oxazoles, with primary photoproducts featuring a reactive cyclic imine moiety suitable for multicomponent postphotochemical transformations. For example, the reaction of these imine photoproducts with bromoacetyl bromide leads to a key 1,4-dielectrophilic...

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Kumar NN, Kutateladze AG. Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent Postphotochemical Multicomponent Modifications. Org Lett. 2016;18(3):460-3doi: 10.1021/acs.orglett.5b03503.
Kumar, N. N., & Kutateladze, A. G. (2016). Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent Postphotochemical Multicomponent Modifications. Organic letters, 18(3), 460-3. https://doi.org/10.1021/acs.orglett.5b03503
Kumar, N N Bhuvan, and Kutateladze, Andrei G. "Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent Postphotochemical Multicomponent Modifications." Organic letters vol. 18,3 (2016): 460-3. doi: https://doi.org/10.1021/acs.orglett.5b03503
Kumar NN, Kutateladze AG. Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent Postphotochemical Multicomponent Modifications. Org Lett. 2016 Feb 05;18(3):460-3. doi: 10.1021/acs.orglett.5b03503. Epub 2016 Jan 13. PMID: 26760049.
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Base-Mediated Cascade Substitution-Cyclization of 2H-Azirines: Access to Highly Substituted Oxazoles.

Organic letters

Duan X, Yang K, Lu J, Kong X, Liu N, Ma J.
PMID: 28605912
Org Lett. 2017 Jul 07;19(13):3370-3373. doi: 10.1021/acs.orglett.7b01305. Epub 2017 Jun 13.

A novel strategy to synthesize highly functionalized oxazoles has been successfully developed via a base-mediated intermolecular substitution between 2-acyloxy-2H-azirines and N-nucleophile or O-nucleophile with a subsequent ring expansion of a 2H-azirine intermediate. This method provides straightforward access to highly...

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Duan X, Yang K, Lu J, et al. Base-Mediated Cascade Substitution-Cyclization of 2H-Azirines: Access to Highly Substituted Oxazoles. Org Lett. 2017;19(13):3370-3373doi: 10.1021/acs.orglett.7b01305.
Duan, X., Yang, K., Lu, J., Kong, X., Liu, N., & Ma, J. (2017). Base-Mediated Cascade Substitution-Cyclization of 2H-Azirines: Access to Highly Substituted Oxazoles. Organic letters, 19(13), 3370-3373. https://doi.org/10.1021/acs.orglett.7b01305
Duan, Xiyan, et al. "Base-Mediated Cascade Substitution-Cyclization of 2H-Azirines: Access to Highly Substituted Oxazoles." Organic letters vol. 19,13 (2017): 3370-3373. doi: https://doi.org/10.1021/acs.orglett.7b01305
Duan X, Yang K, Lu J, Kong X, Liu N, Ma J. Base-Mediated Cascade Substitution-Cyclization of 2H-Azirines: Access to Highly Substituted Oxazoles. Org Lett. 2017 Jul 07;19(13):3370-3373. doi: 10.1021/acs.orglett.7b01305. Epub 2017 Jun 13. PMID: 28605912.
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NOV-002, A Glutathione Disulfide Mimetic, Suppresses Tumor Cell Invasion and Metastasis.

Journal of carcinogenesis & mutagenesis

Gumireddy K, Li A, Cao L, Yan J, Liu L, Xu X, Pazoles C, Huang Q.
PMID: 24377058
J Carcinog Mutagen. 2013 Apr 30;2013. doi: 10.4172/2157-2518.S7-002.

Metastasis is the major cause of death in cancer. Most therapies currently in the clinic aim to eradicate primary tumor, but do not have ideal effects on metastasis. The lack of effective therapy in metastasis prevention and treatment results...

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Gumireddy K, Li A, Cao L, et al. NOV-002, A Glutathione Disulfide Mimetic, Suppresses Tumor Cell Invasion and Metastasis. J Carcinog Mutagen. 2013;2013doi: 10.4172/2157-2518.S7-002.
Gumireddy, K., Li, A., Cao, L., Yan, J., Liu, L., Xu, X., Pazoles, C., & Huang, Q. (2013). NOV-002, A Glutathione Disulfide Mimetic, Suppresses Tumor Cell Invasion and Metastasis. Journal of carcinogenesis & mutagenesis, 2013. https://doi.org/10.4172/2157-2518.S7-002
Gumireddy, Kiranmai, et al. "NOV-002, A Glutathione Disulfide Mimetic, Suppresses Tumor Cell Invasion and Metastasis." Journal of carcinogenesis & mutagenesis vol. 2013 (2013). doi: https://doi.org/10.4172/2157-2518.S7-002
Gumireddy K, Li A, Cao L, Yan J, Liu L, Xu X, Pazoles C, Huang Q. NOV-002, A Glutathione Disulfide Mimetic, Suppresses Tumor Cell Invasion and Metastasis. J Carcinog Mutagen. 2013 Apr 30;2013. doi: 10.4172/2157-2518.S7-002. PMID: 24377058; PMCID: PMC3872994.
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Nickel-Catalyzed C-H Arylation of Benzoxazoles and Oxazoles: Benchmarking the Influence of Electronic, Steric and Leaving Group Variations in Phenolic Electrophiles.

Tetrahedron

Steinberg DF, Turk MC, Kalyani D.
PMID: 29051675
Tetrahedron. 2017 Apr 20;73(16):2196-2209. doi: 10.1016/j.tet.2017.02.021. Epub 2017 Feb 14.

No abstract available.

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Steinberg DF, Turk MC, Kalyani D. Nickel-Catalyzed C-H Arylation of Benzoxazoles and Oxazoles: Benchmarking the Influence of Electronic, Steric and Leaving Group Variations in Phenolic Electrophiles. Tetrahedron. 2017;73(16):2196-2209doi: 10.1016/j.tet.2017.02.021.
Steinberg, D. F., Turk, M. C., & Kalyani, D. (2017). Nickel-Catalyzed C-H Arylation of Benzoxazoles and Oxazoles: Benchmarking the Influence of Electronic, Steric and Leaving Group Variations in Phenolic Electrophiles. Tetrahedron, 73(16), 2196-2209. https://doi.org/10.1016/j.tet.2017.02.021
Steinberg, Deborah F, et al. "Nickel-Catalyzed C-H Arylation of Benzoxazoles and Oxazoles: Benchmarking the Influence of Electronic, Steric and Leaving Group Variations in Phenolic Electrophiles." Tetrahedron vol. 73,16 (2017): 2196-2209. doi: https://doi.org/10.1016/j.tet.2017.02.021
Steinberg DF, Turk MC, Kalyani D. Nickel-Catalyzed C-H Arylation of Benzoxazoles and Oxazoles: Benchmarking the Influence of Electronic, Steric and Leaving Group Variations in Phenolic Electrophiles. Tetrahedron. 2017 Apr 20;73(16):2196-2209. doi: 10.1016/j.tet.2017.02.021. Epub 2017 Feb 14. PMID: 29051675; PMCID: PMC5642964.
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Synthesis of 2,4,5-trisubstituted oxazoles through tin(IV) chloride-mediated reaction of trans-2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates with nitriles.

Chemical communications (Cambridge, England)

Selvi T, Srinivasan K.
PMID: 25090053
Chem Commun (Camb). 2014 Sep 25;50(74):10845-8. doi: 10.1039/c4cc04764h.

trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates when reacted with nitriles in the presence of tin(IV) chloride afford 2,4,5-trisubstituted oxazoles in good to excellent yields. The reactions take place through in situ generation of aroylmethylidene malonates from the cyclopropanes, followed by conjugate addition of nitriles...

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Selvi T, Srinivasan K. Synthesis of 2,4,5-trisubstituted oxazoles through tin(IV) chloride-mediated reaction of trans-2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates with nitriles. Chem Commun (Camb). 2014;50(74):10845-8doi: 10.1039/c4cc04764h.
Selvi, T., & Srinivasan, K. (2014). Synthesis of 2,4,5-trisubstituted oxazoles through tin(IV) chloride-mediated reaction of trans-2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates with nitriles. Chemical communications (Cambridge, England), 50(74), 10845-8. https://doi.org/10.1039/c4cc04764h
Selvi, Thangavel, and Srinivasan, Kannupal. "Synthesis of 2,4,5-trisubstituted oxazoles through tin(IV) chloride-mediated reaction of trans-2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates with nitriles." Chemical communications (Cambridge, England) vol. 50,74 (2014): 10845-8. doi: https://doi.org/10.1039/c4cc04764h
Selvi T, Srinivasan K. Synthesis of 2,4,5-trisubstituted oxazoles through tin(IV) chloride-mediated reaction of trans-2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates with nitriles. Chem Commun (Camb). 2014 Sep 25;50(74):10845-8. doi: 10.1039/c4cc04764h. PMID: 25090053.
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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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A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines.

The Journal of organic chemistry

Padwa A, Brodney MA, Liu B, Satake K, Wu T.
PMID: 11674487
J Org Chem. 1999 May 14;64(10):3595-3607. doi: 10.1021/jo982453g.

The intramolecular Diels-Alder reaction of 2-substituted aminofurans (IMDAF) results in the formation of various indolines and tetrahydroquinolines. The isolation of these ring systems from the IMDAF reaction can be rationalized in terms of an initial [4 + 2]-cycloaddition that...

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Padwa A, Brodney MA, Liu B, et al. A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines. J Org Chem. 1999;64(10):3595-3607doi: 10.1021/jo982453g.
Padwa, A., Brodney, M. A., Liu, B., Satake, K., & Wu, T. (1999). A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines. The Journal of organic chemistry, 64(10), 3595-3607. https://doi.org/10.1021/jo982453g
Padwa, Albert, et al. "A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines." The Journal of organic chemistry vol. 64,10 (1999): 3595-3607. doi: https://doi.org/10.1021/jo982453g
Padwa A, Brodney MA, Liu B, Satake K, Wu T. A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines. J Org Chem. 1999 May 14;64(10):3595-3607. doi: 10.1021/jo982453g. PMID: 11674487.
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Diarylamino groups as photostable auxofluors in 2-benzoxazolylfluorene, 2,5-diphenyloxazoles, 1,3,5-hexatrienes, 1,4-distyrylbenzenes, and 2,7-distyrylfluorenes.

The Journal of organic chemistry

Kauffman JM, Moyna G.
PMID: 12558406
J Org Chem. 2003 Feb 07;68(3):839-53. doi: 10.1021/jo020333+.

The relationship of structure to optical spectral properties was determined for five types of fluors in a search for an optimum-wavelength shifter to be used as part of the detection systems for high-energy particles from accelerators. In a search...

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Kauffman JM, Moyna G. Diarylamino groups as photostable auxofluors in 2-benzoxazolylfluorene, 2,5-diphenyloxazoles, 1,3,5-hexatrienes, 1,4-distyrylbenzenes, and 2,7-distyrylfluorenes. J Org Chem. 2003;68(3):839-53doi: 10.1021/jo020333+.
Kauffman, J. M., & Moyna, G. (2003). Diarylamino groups as photostable auxofluors in 2-benzoxazolylfluorene, 2,5-diphenyloxazoles, 1,3,5-hexatrienes, 1,4-distyrylbenzenes, and 2,7-distyrylfluorenes. The Journal of organic chemistry, 68(3), 839-53. https://doi.org/10.1021/jo020333+
Kauffman, Joel M, and Moyna, Guillermo. "Diarylamino groups as photostable auxofluors in 2-benzoxazolylfluorene, 2,5-diphenyloxazoles, 1,3,5-hexatrienes, 1,4-distyrylbenzenes, and 2,7-distyrylfluorenes." The Journal of organic chemistry vol. 68,3 (2003): 839-53. doi: https://doi.org/10.1021/jo020333+
Kauffman JM, Moyna G. Diarylamino groups as photostable auxofluors in 2-benzoxazolylfluorene, 2,5-diphenyloxazoles, 1,3,5-hexatrienes, 1,4-distyrylbenzenes, and 2,7-distyrylfluorenes. J Org Chem. 2003 Feb 07;68(3):839-53. doi: 10.1021/jo020333+. PMID: 12558406.
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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 187 entries