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Synthesis of substituted imidazoles via organocatalysis.

Organic letters

Frantz DE, Morency L, Soheili A, Murry JA, Grabowski EJ, Tillyer RD.
PMID: 14986989
Org Lett. 2004 Mar 04;6(5):843-6. doi: 10.1021/ol0498803.

A one-pot synthesis of substituted imidazoles is described. The cornerstone of this methodology involves the thiazolium-catalyzed addition of an aldehyde to an acyl imine to generate the corresponding alpha-ketoamide in situ followed by ring closure to the imidazole in...

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Frantz DE, Morency L, Soheili A, et al. Synthesis of substituted imidazoles via organocatalysis. Org Lett. 2004;6(5):843-6doi: 10.1021/ol0498803.
Frantz, D. E., Morency, L., Soheili, A., Murry, J. A., Grabowski, E. J., & Tillyer, R. D. (2004). Synthesis of substituted imidazoles via organocatalysis. Organic letters, 6(5), 843-6. https://doi.org/10.1021/ol0498803
Frantz, Doug E, et al. "Synthesis of substituted imidazoles via organocatalysis." Organic letters vol. 6,5 (2004): 843-6. doi: https://doi.org/10.1021/ol0498803
Frantz DE, Morency L, Soheili A, Murry JA, Grabowski EJ, Tillyer RD. Synthesis of substituted imidazoles via organocatalysis. Org Lett. 2004 Mar 04;6(5):843-6. doi: 10.1021/ol0498803. PMID: 14986989.
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Solid-state packing of conjugated oligomers: from pi-stacks to the herringbone structure.

Journal of the American Chemical Society

Curtis MD, Cao J, Kampf JW.
PMID: 15053622
J Am Chem Soc. 2004 Apr 07;126(13):4318-28. doi: 10.1021/ja0397916.

The solid-state structures of a series of bithiazole and thiophene oligomers, as well as a series of substituted pentacenes, are rationalized in terms of "pitch and roll" inclinations from an "ideal" cofacial pi-stack. Pitch inclinations translate adjacent molecules relative...

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Curtis MD, Cao J, Kampf JW. Solid-state packing of conjugated oligomers: from pi-stacks to the herringbone structure. J Am Chem Soc. 2004;126(13):4318-28doi: 10.1021/ja0397916.
Curtis, M. D., Cao, J., & Kampf, J. W. (2004). Solid-state packing of conjugated oligomers: from pi-stacks to the herringbone structure. Journal of the American Chemical Society, 126(13), 4318-28. https://doi.org/10.1021/ja0397916
Curtis, M David, et al. "Solid-state packing of conjugated oligomers: from pi-stacks to the herringbone structure." Journal of the American Chemical Society vol. 126,13 (2004): 4318-28. doi: https://doi.org/10.1021/ja0397916
Curtis MD, Cao J, Kampf JW. Solid-state packing of conjugated oligomers: from pi-stacks to the herringbone structure. J Am Chem Soc. 2004 Apr 07;126(13):4318-28. doi: 10.1021/ja0397916. PMID: 15053622.
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On the [2+2] cycloaddition of 2-aminothiazoles and dimethyl acetylenedicarboxylate. Experimental and computational evidence of a thermal disrotatory ring opening of fused cyclobutenes.

The Journal of organic chemistry

Alajarín M, Cabrera J, Pastor A, Sanchez-Andrada P, Bautista D.
PMID: 16808523
J Org Chem. 2006 Jul 07;71(14):5328-39. doi: 10.1021/jo060664c.

The reaction of 2-(phenylamino)- and 2-(dimethylamino)thiazoles with dimethyl acetylenedicarboxylate led unexpectedly to dimethyl 6-(phenylamino)- and 6-(dimethylamino)-3,4-pyridinedicarboxylates. Those compounds reasonably result from a sequence of reactions initiated by a [2 + 2] cycloaddition of the alkyne to the formal C=C...

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Alajarín M, Cabrera J, Pastor A, et al. On the [2+2] cycloaddition of 2-aminothiazoles and dimethyl acetylenedicarboxylate. Experimental and computational evidence of a thermal disrotatory ring opening of fused cyclobutenes. J Org Chem. 2006;71(14):5328-39doi: 10.1021/jo060664c.
Alajarín, M., Cabrera, J., Pastor, A., Sanchez-Andrada, P., & Bautista, D. (2006). On the [2+2] cycloaddition of 2-aminothiazoles and dimethyl acetylenedicarboxylate. Experimental and computational evidence of a thermal disrotatory ring opening of fused cyclobutenes. The Journal of organic chemistry, 71(14), 5328-39. https://doi.org/10.1021/jo060664c
Alajarín, Mateo, et al. "On the [2+2] cycloaddition of 2-aminothiazoles and dimethyl acetylenedicarboxylate. Experimental and computational evidence of a thermal disrotatory ring opening of fused cyclobutenes." The Journal of organic chemistry vol. 71,14 (2006): 5328-39. doi: https://doi.org/10.1021/jo060664c
Alajarín M, Cabrera J, Pastor A, Sanchez-Andrada P, Bautista D. On the [2+2] cycloaddition of 2-aminothiazoles and dimethyl acetylenedicarboxylate. Experimental and computational evidence of a thermal disrotatory ring opening of fused cyclobutenes. J Org Chem. 2006 Jul 07;71(14):5328-39. doi: 10.1021/jo060664c. PMID: 16808523.
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1H, 13C and 15N NMR studies on adducts formation of rhodium(II) tetraacylates with some azoles in CDCl3 solution.

Magnetic resonance in chemistry : MRC

Bocian W, Jaźwiński J, Sadlej A.
PMID: 18088083
Magn Reson Chem. 2008 Feb;46(2):156-65. doi: 10.1002/mrc.2149.

Adduct formations of rhodium(II) tetraacetate and tetratrifluoroacetate with some 1H-imidazoles, oxazoles, thiazoles, 1H-pyrazoles and isoxazole have been investigated by the use of 1H, 13C, 15N NMR and electronic absorption spectroscopy (VIS) in the visible range. Azoles tend to form...

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Bocian W, Jaźwiński J, Sadlej A. 1H, 13C and 15N NMR studies on adducts formation of rhodium(II) tetraacylates with some azoles in CDCl3 solution. Magn Reson Chem. 2008;46(2):156-65doi: 10.1002/mrc.2149.
Bocian, W., Jaźwiński, J., & Sadlej, A. (2008). 1H, 13C and 15N NMR studies on adducts formation of rhodium(II) tetraacylates with some azoles in CDCl3 solution. Magnetic resonance in chemistry : MRC, 46(2), 156-65. https://doi.org/10.1002/mrc.2149
Bocian, Wojciech, et al. "1H, 13C and 15N NMR studies on adducts formation of rhodium(II) tetraacylates with some azoles in CDCl3 solution." Magnetic resonance in chemistry : MRC vol. 46,2 (2008): 156-65. doi: https://doi.org/10.1002/mrc.2149
Bocian W, Jaźwiński J, Sadlej A. 1H, 13C and 15N NMR studies on adducts formation of rhodium(II) tetraacylates with some azoles in CDCl3 solution. Magn Reson Chem. 2008 Feb;46(2):156-65. doi: 10.1002/mrc.2149. PMID: 18088083.
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Asymmetric hydrogenation of trisubstituted olefins with iridium-phosphine thiazole complexes: a further investigation of the ligand structure.

Journal of the American Chemical Society

Hedberg C, Källström K, Brandt P, Hansen LK, Andersson PG.
PMID: 16506780
J Am Chem Soc. 2006 Mar 08;128(9):2995-3001. doi: 10.1021/ja057178b.

New chiral bidentate phoshine thiazoles have been prepared and successfully applied as ligands in the homogeneous iridium-catalyzed asymmetric hydrogenation of aryl alkenes and aryl alkene esters. The ligands are designed to be highly modular and have one common chiral...

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Hedberg C, Källström K, Brandt P, et al. Asymmetric hydrogenation of trisubstituted olefins with iridium-phosphine thiazole complexes: a further investigation of the ligand structure. J Am Chem Soc. 2006;128(9):2995-3001doi: 10.1021/ja057178b.
Hedberg, C., Källström, K., Brandt, P., Hansen, L. K., & Andersson, P. G. (2006). Asymmetric hydrogenation of trisubstituted olefins with iridium-phosphine thiazole complexes: a further investigation of the ligand structure. Journal of the American Chemical Society, 128(9), 2995-3001. https://doi.org/10.1021/ja057178b
Hedberg, Christian, et al. "Asymmetric hydrogenation of trisubstituted olefins with iridium-phosphine thiazole complexes: a further investigation of the ligand structure." Journal of the American Chemical Society vol. 128,9 (2006): 2995-3001. doi: https://doi.org/10.1021/ja057178b
Hedberg C, Källström K, Brandt P, Hansen LK, Andersson PG. Asymmetric hydrogenation of trisubstituted olefins with iridium-phosphine thiazole complexes: a further investigation of the ligand structure. J Am Chem Soc. 2006 Mar 08;128(9):2995-3001. doi: 10.1021/ja057178b. PMID: 16506780.
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Coumarinyl(thienyl)thiazoles: novel photochromes with modulated fluorescence.

Organic letters

Traven VF, Bochkov AY, Krayushkin MM, Yarovenko VN, Nabatov BV, Dolotov SM, Barachevsky VA, Beletskaya IP.
PMID: 18303909
Org Lett. 2008 Mar 20;10(6):1319-22. doi: 10.1021/ol800223g. Epub 2008 Feb 28.

Novel photochromic 5-(3'-coumarinyl)-4-(3''-thienyl)thiazoles have been synthesized. These compounds display intensive fluorescence emission in the open form A, which is modulated by light. Fluorescence intensity decreases significantly upon irradiation of A with UV-light (lambda470 nm) promotes its opening and the...

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Traven VF, Bochkov AY, Krayushkin MM, et al. Coumarinyl(thienyl)thiazoles: novel photochromes with modulated fluorescence. Org Lett. 2008;10(6):1319-22doi: 10.1021/ol800223g.
Traven, V. F., Bochkov, A. Y., Krayushkin, M. M., Yarovenko, V. N., Nabatov, B. V., Dolotov, S. M., Barachevsky, V. A., & Beletskaya, I. P. (2008). Coumarinyl(thienyl)thiazoles: novel photochromes with modulated fluorescence. Organic letters, 10(6), 1319-22. https://doi.org/10.1021/ol800223g
Traven, Valery F, et al. "Coumarinyl(thienyl)thiazoles: novel photochromes with modulated fluorescence." Organic letters vol. 10,6 (2008): 1319-22. doi: https://doi.org/10.1021/ol800223g
Traven VF, Bochkov AY, Krayushkin MM, Yarovenko VN, Nabatov BV, Dolotov SM, Barachevsky VA, Beletskaya IP. Coumarinyl(thienyl)thiazoles: novel photochromes with modulated fluorescence. Org Lett. 2008 Mar 20;10(6):1319-22. doi: 10.1021/ol800223g. Epub 2008 Feb 28. PMID: 18303909.
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Microwave-assisted Heterocyclic Dicarboxylic Acids as Potential Antifungal and Antibacterial Drugs.

Indian journal of pharmaceutical sciences

Dabholkar VV, Parab SD.
PMID: 22303064
Indian J Pharm Sci. 2011 Mar;73(2):199-207. doi: 10.4103/0250-474x.91581.

A series of new dicarboxylic acid derivatives of 1,3,4-thiadiazines, 1,4-benzopiperizines, 1,4-thiazines, 1,3-thiazoles, 1,3-oxazoles and 1,3-imidazoles have been synthesized in 80-87% yield by the environmentally benign microwave induced technique involving the cyclocondensation of 2,3-dibromosuccinic acid with 2-aminothiophenol, o-phenylene diamine, 1,2,4-triazole,...

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Dabholkar VV, Parab SD. Microwave-assisted Heterocyclic Dicarboxylic Acids as Potential Antifungal and Antibacterial Drugs. Indian J Pharm Sci. 2011;73(2):199-207doi: 10.4103/0250-474x.91581.
Dabholkar, V. V., & Parab, S. D. (2011). Microwave-assisted Heterocyclic Dicarboxylic Acids as Potential Antifungal and Antibacterial Drugs. Indian journal of pharmaceutical sciences, 73(2), 199-207. https://doi.org/10.4103/0250-474x.91581
Dabholkar, V V, and Parab, S D. "Microwave-assisted Heterocyclic Dicarboxylic Acids as Potential Antifungal and Antibacterial Drugs." Indian journal of pharmaceutical sciences vol. 73,2 (2011): 199-207. doi: https://doi.org/10.4103/0250-474x.91581
Dabholkar VV, Parab SD. Microwave-assisted Heterocyclic Dicarboxylic Acids as Potential Antifungal and Antibacterial Drugs. Indian J Pharm Sci. 2011 Mar;73(2):199-207. doi: 10.4103/0250-474x.91581. PMID: 22303064; PMCID: PMC3267305.
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Synthesis of 2,4-disubstituted thiazoles from (Z)-(2-acetoxyvinyl)phenyl-lambda3-iodanes: nucleophilic substitution of alpha-lambda3-iodanyl ketones with thioureas and thioamides.

The Journal of organic chemistry

Ochiai M, Nishi Y, Hashimoto S, Tsuchimoto Y, Chen DW.
PMID: 14510572
J Org Chem. 2003 Oct 03;68(20):7887-8. doi: 10.1021/jo020759o.

In the presence of triethylamine, (Z)-(2-acetoxy-1-alkenyl)phenyl-lambda(3)-iodanes react with thioureas or thioamides in MeOH to give 2,4-disubstituted thiazoles directly in good yields. The reaction probably involves generation of highly reactive alpha-lambda(3)-iodanyl ketones through ester exchange of the beta-acetoxy group with...

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Ochiai M, Nishi Y, Hashimoto S, et al. Synthesis of 2,4-disubstituted thiazoles from (Z)-(2-acetoxyvinyl)phenyl-lambda3-iodanes: nucleophilic substitution of alpha-lambda3-iodanyl ketones with thioureas and thioamides. J Org Chem. 2003;68(20):7887-8doi: 10.1021/jo020759o.
Ochiai, M., Nishi, Y., Hashimoto, S., Tsuchimoto, Y., & Chen, D. W. (2003). Synthesis of 2,4-disubstituted thiazoles from (Z)-(2-acetoxyvinyl)phenyl-lambda3-iodanes: nucleophilic substitution of alpha-lambda3-iodanyl ketones with thioureas and thioamides. The Journal of organic chemistry, 68(20), 7887-8. https://doi.org/10.1021/jo020759o
Ochiai, Masahito, et al. "Synthesis of 2,4-disubstituted thiazoles from (Z)-(2-acetoxyvinyl)phenyl-lambda3-iodanes: nucleophilic substitution of alpha-lambda3-iodanyl ketones with thioureas and thioamides." The Journal of organic chemistry vol. 68,20 (2003): 7887-8. doi: https://doi.org/10.1021/jo020759o
Ochiai M, Nishi Y, Hashimoto S, Tsuchimoto Y, Chen DW. Synthesis of 2,4-disubstituted thiazoles from (Z)-(2-acetoxyvinyl)phenyl-lambda3-iodanes: nucleophilic substitution of alpha-lambda3-iodanyl ketones with thioureas and thioamides. J Org Chem. 2003 Oct 03;68(20):7887-8. doi: 10.1021/jo020759o. PMID: 14510572.
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Substituted 2-[(2-Oxo-2H-[1,2,4]triazino [2,3-c]quinazolin-6-yl)thio]acetamides with Thiazole and Thiadiazole Fragments: Synthesis, Physicochemical Properties, Cytotoxicity, and Anticancer Activity.

Scientia pharmaceutica

Kovalenko SI, Nosulenko IS, Voskoboynik AY, Berest GG, Antypenko LN, Antypenko AN, Katsev AM.
PMID: 23264935
Sci Pharm. 2012 Oct-Dec;80(4):837-65. doi: 10.3797/scipharm.1208-07. Epub 2012 Oct 04.

The series of novel N-R-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazolin-6-yl)thio]acetamides with thiazole and thiadiazole fragments in a molecule were obtained by alkylation of potassium salts 1.1-1.4 by N-hetaryl-2-chloroacetamides and by aminolysis of activated acids 2.1-2.4 with N,N'-carbonyldiimidazole (CDI). The structures of compounds were determined...

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Kovalenko SI, Nosulenko IS, Voskoboynik AY, et al. Substituted 2-[(2-Oxo-2H-[1,2,4]triazino [2,3-c]quinazolin-6-yl)thio]acetamides with Thiazole and Thiadiazole Fragments: Synthesis, Physicochemical Properties, Cytotoxicity, and Anticancer Activity. Sci Pharm. 2012;80(4):837-65doi: 10.3797/scipharm.1208-07.
Kovalenko, S. I., Nosulenko, I. S., Voskoboynik, A. Y., Berest, G. G., Antypenko, L. N., Antypenko, A. N., & Katsev, A. M. (2012). Substituted 2-[(2-Oxo-2H-[1,2,4]triazino [2,3-c]quinazolin-6-yl)thio]acetamides with Thiazole and Thiadiazole Fragments: Synthesis, Physicochemical Properties, Cytotoxicity, and Anticancer Activity. Scientia pharmaceutica, 80(4), 837-65. https://doi.org/10.3797/scipharm.1208-07
Kovalenko, Sergey I, et al. "Substituted 2-[(2-Oxo-2H-[1,2,4]triazino [2,3-c]quinazolin-6-yl)thio]acetamides with Thiazole and Thiadiazole Fragments: Synthesis, Physicochemical Properties, Cytotoxicity, and Anticancer Activity." Scientia pharmaceutica vol. 80,4 (2012): 837-65. doi: https://doi.org/10.3797/scipharm.1208-07
Kovalenko SI, Nosulenko IS, Voskoboynik AY, Berest GG, Antypenko LN, Antypenko AN, Katsev AM. Substituted 2-[(2-Oxo-2H-[1,2,4]triazino [2,3-c]quinazolin-6-yl)thio]acetamides with Thiazole and Thiadiazole Fragments: Synthesis, Physicochemical Properties, Cytotoxicity, and Anticancer Activity. Sci Pharm. 2012 Oct-Dec;80(4):837-65. doi: 10.3797/scipharm.1208-07. Epub 2012 Oct 04. PMID: 23264935; PMCID: PMC3528059.
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Synthesis and anti-tubercular activity of 3-substituted benzo[b]thiophene-1,1-dioxides.

PeerJ

Chandrasekera NS, Bailey MA, Files M, Alling T, Florio SK, Ollinger J, Odingo JO, Parish T.
PMID: 25320680
PeerJ. 2014 Oct 07;2:e612. doi: 10.7717/peerj.612. eCollection 2014.

We demonstrated that the 3-substituted benzothiophene-1,1-dioxide class of compounds are effective inhibitors of Mycobacterium tuberculosis growth under aerobic conditions. We examined substitution at the C-3 position of the benzothiophene-1,1-dioxide series systematically to delineate structure-activity relationships influencing potency and cytotoxicity....

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Chandrasekera NS, Bailey MA, Files M, et al. Synthesis and anti-tubercular activity of 3-substituted benzo[b]thiophene-1,1-dioxides. PeerJ. 2014;2:e612doi: 10.7717/peerj.612.
Chandrasekera, N. S., Bailey, M. A., Files, M., Alling, T., Florio, S. K., Ollinger, J., Odingo, J. O., & Parish, T. (2014). Synthesis and anti-tubercular activity of 3-substituted benzo[b]thiophene-1,1-dioxides. PeerJ, 2e612. https://doi.org/10.7717/peerj.612
Chandrasekera, N Susantha, et al. "Synthesis and anti-tubercular activity of 3-substituted benzo[b]thiophene-1,1-dioxides." PeerJ vol. 2 (2014): e612. doi: https://doi.org/10.7717/peerj.612
Chandrasekera NS, Bailey MA, Files M, Alling T, Florio SK, Ollinger J, Odingo JO, Parish T. Synthesis and anti-tubercular activity of 3-substituted benzo[b]thiophene-1,1-dioxides. PeerJ. 2014 Oct 07;2:e612. doi: 10.7717/peerj.612. eCollection 2014. PMID: 25320680; PMCID: PMC4193402.
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Enantioselective recognition of carboxylic acids by novel fluorescent triazine-based thiazoles.

Chirality

Halay E, Bozkurt S.
PMID: 29210117
Chirality. 2018 Mar;30(3):275-283. doi: 10.1002/chir.22792. Epub 2017 Dec 06.

Hydrogen bonding and π-π interactions take special part in the enantioselectivity task. In this regard, because of having both hydrogen acceptor and hydrogen donor groups, melamine derivatives become more of an issue for enantioselectivity. In the light of such...

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Halay E, Bozkurt S. Enantioselective recognition of carboxylic acids by novel fluorescent triazine-based thiazoles. Chirality. 2017;30(3):275-283doi: 10.1002/chir.22792.
Halay, E., & Bozkurt, S. (2018). Enantioselective recognition of carboxylic acids by novel fluorescent triazine-based thiazoles. Chirality, 30(3), 275-283. https://doi.org/10.1002/chir.22792
Halay, Erkan, and Bozkurt, Selahattin. "Enantioselective recognition of carboxylic acids by novel fluorescent triazine-based thiazoles." Chirality vol. 30,3 (2018): 275-283. doi: https://doi.org/10.1002/chir.22792
Halay E, Bozkurt S. Enantioselective recognition of carboxylic acids by novel fluorescent triazine-based thiazoles. Chirality. 2018 Mar;30(3):275-283. doi: 10.1002/chir.22792. Epub 2017 Dec 06. PMID: 29210117.
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Synthesis of N,S-Heterocycles and Dithiocarbamates by the Reaction of Dithiocarbamic Acids and S-Alkyl Dithiocarbamates with Nitroepoxides.

Organic letters

Ziyaei Halimehjani A, Lotfi Nosood Y.
PMID: 29210274
Org Lett. 2017 Dec 15;19(24):6748-6751. doi: 10.1021/acs.orglett.7b03501. Epub 2017 Dec 06.

A facile and efficient procedure for the synthesis of substituted thiazole-2(3H)-thiones and thiazolidine-2-thiones by the reaction of primary amines, carbon disulfide, and nitroepoxides is described. By using secondary amines in this protocol, the corresponding dithiocarbamate-substituted phenyl-2-propanones were prepared in...

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Ziyaei Halimehjani A, Lotfi Nosood Y. Synthesis of N,S-Heterocycles and Dithiocarbamates by the Reaction of Dithiocarbamic Acids and S-Alkyl Dithiocarbamates with Nitroepoxides. Org Lett. 2017;19(24):6748-6751doi: 10.1021/acs.orglett.7b03501.
Ziyaei Halimehjani, A., & Lotfi Nosood, Y. (2017). Synthesis of N,S-Heterocycles and Dithiocarbamates by the Reaction of Dithiocarbamic Acids and S-Alkyl Dithiocarbamates with Nitroepoxides. Organic letters, 19(24), 6748-6751. https://doi.org/10.1021/acs.orglett.7b03501
Ziyaei Halimehjani, Azim, and Lotfi Nosood, Yazdanbakhsh. "Synthesis of N,S-Heterocycles and Dithiocarbamates by the Reaction of Dithiocarbamic Acids and S-Alkyl Dithiocarbamates with Nitroepoxides." Organic letters vol. 19,24 (2017): 6748-6751. doi: https://doi.org/10.1021/acs.orglett.7b03501
Ziyaei Halimehjani A, Lotfi Nosood Y. Synthesis of N,S-Heterocycles and Dithiocarbamates by the Reaction of Dithiocarbamic Acids and S-Alkyl Dithiocarbamates with Nitroepoxides. Org Lett. 2017 Dec 15;19(24):6748-6751. doi: 10.1021/acs.orglett.7b03501. Epub 2017 Dec 06. PMID: 29210274.
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