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5-(Methylthio)tetrazoles as Versatile Synthons in the Stereoselective Synthesis of Polycyclic Pyrazolines via Photoinduced Intramolecular Nitrile Imine-Alkene 1,3-Dipolar Cycloaddition.

Chemical science

Pla D, Tan DS, Gin DY.
PMID: 25114776
Chem Sci. 2014 Jun 01;5(6):2407-2415. doi: 10.1039/C4SC00107A.

A key thioether substituent in readily accessible 2-alkyl-5-(methylthio)tetrazoles enables facile photoinduced denitrogenation and intramolecular nitrile imine 1,3-dipolar cycloaddition to afford a wide range of polycyclic pyrazoline products with excellent diastereoselectivity. The methylthio group red-shifts the UV absorbance of the...

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Pla D, Tan DS, Gin DY. 5-(Methylthio)tetrazoles as Versatile Synthons in the Stereoselective Synthesis of Polycyclic Pyrazolines via Photoinduced Intramolecular Nitrile Imine-Alkene 1,3-Dipolar Cycloaddition. Chem Sci. 2014;5(6):2407-2415doi: 10.1039/C4SC00107A.
Pla, D., Tan, D. S., & Gin, D. Y. (2014). 5-(Methylthio)tetrazoles as Versatile Synthons in the Stereoselective Synthesis of Polycyclic Pyrazolines via Photoinduced Intramolecular Nitrile Imine-Alkene 1,3-Dipolar Cycloaddition. Chemical science, 5(6), 2407-2415. https://doi.org/10.1039/C4SC00107A
Pla, Daniel, et al. "5-(Methylthio)tetrazoles as Versatile Synthons in the Stereoselective Synthesis of Polycyclic Pyrazolines via Photoinduced Intramolecular Nitrile Imine-Alkene 1,3-Dipolar Cycloaddition." Chemical science vol. 5,6 (2014): 2407-2415. doi: https://doi.org/10.1039/C4SC00107A
Pla D, Tan DS, Gin DY. 5-(Methylthio)tetrazoles as Versatile Synthons in the Stereoselective Synthesis of Polycyclic Pyrazolines via Photoinduced Intramolecular Nitrile Imine-Alkene 1,3-Dipolar Cycloaddition. Chem Sci. 2014 Jun 01;5(6):2407-2415. doi: 10.1039/C4SC00107A. PMID: 25114776; PMCID: PMC4126266.
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C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles.

The Journal of organic chemistry

Wentrup C, Becker J, Diehl M.
PMID: 26086716
J Org Chem. 2015 Jul 17;80(14):7144-9. doi: 10.1021/acs.joc.5b01007. Epub 2015 Jun 26.

2-Phenyl-5-(phenylethynyl)tetrazole 44 provides a new entry to the C15H10 energy surface. Flash vacuum pyrolysis of 44 using the falling solid flash vacuum pyrolysis (FS-FVP) method afforded cyclopenta[def]phenanthrene 31 and cyclopenta[jk]fluorene 52 as the principal products. The products are explained...

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Wentrup C, Becker J, Diehl M. C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles. J Org Chem. 2015;80(14):7144-9doi: 10.1021/acs.joc.5b01007.
Wentrup, C., Becker, J., & Diehl, M. (2015). C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles. The Journal of organic chemistry, 80(14), 7144-9. https://doi.org/10.1021/acs.joc.5b01007
Wentrup, Curt, et al. "C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles." The Journal of organic chemistry vol. 80,14 (2015): 7144-9. doi: https://doi.org/10.1021/acs.joc.5b01007
Wentrup C, Becker J, Diehl M. C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles. J Org Chem. 2015 Jul 17;80(14):7144-9. doi: 10.1021/acs.joc.5b01007. Epub 2015 Jun 26. PMID: 26086716.
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Uncovering the Role of Metal Catalysis in Tetrazole Formation by an In Situ Cycloaddition Reaction: An Experimental Approach.

Angewandte Chemie (International ed. in English)

Zhong DC, Wen YQ, Deng JH, Luo XZ, Gong YN, Lu TB.
PMID: 26293313
Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11795-9. doi: 10.1002/anie.201505118. Epub 2015 Aug 18.

Using an experimental approach, the role of metal catalysis has been investigated in the in situ cycloaddition reaction of nitrile with azide to form tetrazoles. It has been shown that metal catalysis serves to activate the cyano group in...

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Zhong DC, Wen YQ, Deng JH, et al. Uncovering the Role of Metal Catalysis in Tetrazole Formation by an In Situ Cycloaddition Reaction: An Experimental Approach. Angew Chem Int Ed Engl. 2015;54(40):11795-9doi: 10.1002/anie.201505118.
Zhong, D. C., Wen, Y. Q., Deng, J. H., Luo, X. Z., Gong, Y. N., & Lu, T. B. (2015). Uncovering the Role of Metal Catalysis in Tetrazole Formation by an In Situ Cycloaddition Reaction: An Experimental Approach. Angewandte Chemie (International ed. in English), 54(40), 11795-9. https://doi.org/10.1002/anie.201505118
Zhong, Di-Chang, et al. "Uncovering the Role of Metal Catalysis in Tetrazole Formation by an In Situ Cycloaddition Reaction: An Experimental Approach." Angewandte Chemie (International ed. in English) vol. 54,40 (2015): 11795-9. doi: https://doi.org/10.1002/anie.201505118
Zhong DC, Wen YQ, Deng JH, Luo XZ, Gong YN, Lu TB. Uncovering the Role of Metal Catalysis in Tetrazole Formation by an In Situ Cycloaddition Reaction: An Experimental Approach. Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11795-9. doi: 10.1002/anie.201505118. Epub 2015 Aug 18. PMID: 26293313.
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Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates.

The Journal of organic chemistry

Yoneyama H, Numata M, Uemura K, Usami Y, Harusawa S.
PMID: 28470066
J Org Chem. 2017 Jun 02;82(11):5538-5556. doi: 10.1021/acs.joc.7b00346. Epub 2017 May 17.

Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN

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Yoneyama H, Numata M, Uemura K, et al. Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates. J Org Chem. 2017;82(11):5538-5556doi: 10.1021/acs.joc.7b00346.
Yoneyama, H., Numata, M., Uemura, K., Usami, Y., & Harusawa, S. (2017). Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates. The Journal of organic chemistry, 82(11), 5538-5556. https://doi.org/10.1021/acs.joc.7b00346
Yoneyama, Hiroki, et al. "Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates." The Journal of organic chemistry vol. 82,11 (2017): 5538-5556. doi: https://doi.org/10.1021/acs.joc.7b00346
Yoneyama H, Numata M, Uemura K, Usami Y, Harusawa S. Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates. J Org Chem. 2017 Jun 02;82(11):5538-5556. doi: 10.1021/acs.joc.7b00346. Epub 2017 May 17. PMID: 28470066.
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Enantioselective formation of tertiary and quaternary allylic C-N bonds via allylation of tetrazoles.

Chemical communications (Cambridge, England)

Xu K, Raimondi W, Bury T, Breit B.
PMID: 26051122
Chem Commun (Camb). 2015 Jul 11;51(54):10861-3. doi: 10.1039/c5cc04203h.

Rhodium-catalyzed regio- and enantioselective coupling of tetrazoles with allenes are reported. Asymmetric construction of tertiary and quaternary allylic C-N bonds were achieved using a Rh(I)/JoSPOphos catalyst. This method permits the atom-economic synthesis of various valuable N(2)-allylic tetrazoles.

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Xu K, Raimondi W, Bury T, et al. Enantioselective formation of tertiary and quaternary allylic C-N bonds via allylation of tetrazoles. Chem Commun (Camb). 2015;51(54):10861-3doi: 10.1039/c5cc04203h.
Xu, K., Raimondi, W., Bury, T., & Breit, B. (2015). Enantioselective formation of tertiary and quaternary allylic C-N bonds via allylation of tetrazoles. Chemical communications (Cambridge, England), 51(54), 10861-3. https://doi.org/10.1039/c5cc04203h
Xu, Kun, et al. "Enantioselective formation of tertiary and quaternary allylic C-N bonds via allylation of tetrazoles." Chemical communications (Cambridge, England) vol. 51,54 (2015): 10861-3. doi: https://doi.org/10.1039/c5cc04203h
Xu K, Raimondi W, Bury T, Breit B. Enantioselective formation of tertiary and quaternary allylic C-N bonds via allylation of tetrazoles. Chem Commun (Camb). 2015 Jul 11;51(54):10861-3. doi: 10.1039/c5cc04203h. PMID: 26051122.
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Parallel Synthesis of Alkyl Tetrazole Derivatives Using Solid Support Chemistry.

Journal of combinatorial chemistry

Matthews DP, Green JE, Shuker AJ.
PMID: 10813880
J Comb Chem. 2000 Jan 11;2(1):19-23. doi: 10.1021/cc990035z.

The synthesis of several omega-chloroalkyl tetrazoles and their subsequent attachment to a solid support is described. Using an in situ Finkelstein reaction, a variety of nucleophiles were alkylated and then cleaved from the resin to give pure alkyl tetrazole...

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Matthews DP, Green JE, Shuker AJ. Parallel Synthesis of Alkyl Tetrazole Derivatives Using Solid Support Chemistry. J Comb Chem. 2000;2(1):19-23doi: 10.1021/cc990035z.
Matthews, D. P., Green, J. E., & Shuker, A. J. (2000). Parallel Synthesis of Alkyl Tetrazole Derivatives Using Solid Support Chemistry. Journal of combinatorial chemistry, 2(1), 19-23. https://doi.org/10.1021/cc990035z
Matthews, et al. "Parallel Synthesis of Alkyl Tetrazole Derivatives Using Solid Support Chemistry." Journal of combinatorial chemistry vol. 2,1 (2000): 19-23. doi: https://doi.org/10.1021/cc990035z
Matthews DP, Green JE, Shuker AJ. Parallel Synthesis of Alkyl Tetrazole Derivatives Using Solid Support Chemistry. J Comb Chem. 2000 Jan 11;2(1):19-23. doi: 10.1021/cc990035z. PMID: 10813880.
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Direct conversion of aldehydes to amides, tetrazoles, and triazines in aqueous media by one-pot tandem reactions.

The Journal of organic chemistry

Shie JJ, Fang JM.
PMID: 12558451
J Org Chem. 2003 Feb 07;68(3):1158-60. doi: 10.1021/jo026407z.

A variety of aldehydes reacted with iodine in ammonia water at room temperature to give the nitrile intermediates, which were trapped by addition of hydrogen peroxide, sodium azide, or dicyandiamide to produce their corresponding amides, tetrazoles, and 1,3,5-triazines in...

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Shie JJ, Fang JM. Direct conversion of aldehydes to amides, tetrazoles, and triazines in aqueous media by one-pot tandem reactions. J Org Chem. 2003;68(3):1158-60doi: 10.1021/jo026407z.
Shie, J. J., & Fang, J. M. (2003). Direct conversion of aldehydes to amides, tetrazoles, and triazines in aqueous media by one-pot tandem reactions. The Journal of organic chemistry, 68(3), 1158-60. https://doi.org/10.1021/jo026407z
Shie, Jiun-Jie, and Fang, Jim-Min. "Direct conversion of aldehydes to amides, tetrazoles, and triazines in aqueous media by one-pot tandem reactions." The Journal of organic chemistry vol. 68,3 (2003): 1158-60. doi: https://doi.org/10.1021/jo026407z
Shie JJ, Fang JM. Direct conversion of aldehydes to amides, tetrazoles, and triazines in aqueous media by one-pot tandem reactions. J Org Chem. 2003 Feb 07;68(3):1158-60. doi: 10.1021/jo026407z. PMID: 12558451.
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Synthesis and characterization of 5-(1,2,4-triazol-3-yl)tetrazoles with various energetic functionalities.

Chemistry, an Asian journal

Dippold AA, Klapötke TM.
PMID: 23630043
Chem Asian J. 2013 Jul;8(7):1463-71. doi: 10.1002/asia.201300063. Epub 2013 Apr 29.

In this contribution the synthesis and full structural as well as spectroscopic characterization of three 5-(1,2,4-triazol-3-yl)tetrazoles along with selected energetic moieties like nitro, nitrimino, and azido groups are presented. The main goal is a comparative study on the influence...

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Dippold AA, Klapötke TM. Synthesis and characterization of 5-(1,2,4-triazol-3-yl)tetrazoles with various energetic functionalities. Chem Asian J. 2013;8(7):1463-71doi: 10.1002/asia.201300063.
Dippold, A. A., & Klapötke, T. M. (2013). Synthesis and characterization of 5-(1,2,4-triazol-3-yl)tetrazoles with various energetic functionalities. Chemistry, an Asian journal, 8(7), 1463-71. https://doi.org/10.1002/asia.201300063
Dippold, Alexander A, and Klapötke, Thomas M. "Synthesis and characterization of 5-(1,2,4-triazol-3-yl)tetrazoles with various energetic functionalities." Chemistry, an Asian journal vol. 8,7 (2013): 1463-71. doi: https://doi.org/10.1002/asia.201300063
Dippold AA, Klapötke TM. Synthesis and characterization of 5-(1,2,4-triazol-3-yl)tetrazoles with various energetic functionalities. Chem Asian J. 2013 Jul;8(7):1463-71. doi: 10.1002/asia.201300063. Epub 2013 Apr 29. PMID: 23630043.
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Ferric Hydrogensulfate [Fe(HSO4)3] As a Reusable Heterogeneous Catalyst for the Synthesis of 5-Substituted-1H-Tetrazoles and Amides.

ISRN organic chemistry

Eshghi H, Seyedi SM, Zarei ER.
PMID: 24052817
ISRN Org Chem. 2011 Mar 29;2011:195850. doi: 10.5402/2011/195850. eCollection 2011.

Ferric hydrogensulfate catalyzed the synthesis of 5-substituted 1H-tetrazoles via [2 + 3] cycloaddition of nitriles and sodium azide. This method has the advantages of high yields, simple methodology, and easy workup. The catalyst can be recovered by simple filtration...

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Eshghi H, Seyedi SM, Zarei ER. Ferric Hydrogensulfate [Fe(HSO4)3] As a Reusable Heterogeneous Catalyst for the Synthesis of 5-Substituted-1H-Tetrazoles and Amides. ISRN Org Chem. 2011;2011:195850doi: 10.5402/2011/195850.
Eshghi, H., Seyedi, S. M., & Zarei, E. R. (2011). Ferric Hydrogensulfate [Fe(HSO4)3] As a Reusable Heterogeneous Catalyst for the Synthesis of 5-Substituted-1H-Tetrazoles and Amides. ISRN organic chemistry, 2011195850. https://doi.org/10.5402/2011/195850
Eshghi, Hossein, et al. "Ferric Hydrogensulfate [Fe(HSO4)3] As a Reusable Heterogeneous Catalyst for the Synthesis of 5-Substituted-1H-Tetrazoles and Amides." ISRN organic chemistry vol. 2011 (2011): 195850. doi: https://doi.org/10.5402/2011/195850
Eshghi H, Seyedi SM, Zarei ER. Ferric Hydrogensulfate [Fe(HSO4)3] As a Reusable Heterogeneous Catalyst for the Synthesis of 5-Substituted-1H-Tetrazoles and Amides. ISRN Org Chem. 2011 Mar 29;2011:195850. doi: 10.5402/2011/195850. eCollection 2011. PMID: 24052817; PMCID: PMC3767363.
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Synthesis, structure, and properties of group 1 metal complexes containing nitrogen-rich hydrotris(tetrazolyl)borate ligands.

Chemistry (Weinheim an der Bergstrasse, Germany)

Snyder CJ, Martin PD, Heeg MJ, Winter CH.
PMID: 23386471
Chemistry. 2013 Mar 04;19(10):3306-10. doi: 10.1002/chem.201203990. Epub 2013 Feb 05.

Nitrogen-rich hydrotris(tetrazolyl)borate salts of lithium, sodium, and potassium have been prepared for the first time by thermolysis of the borohydride ion with three equivalents of tetrazoles in ether solvents at 160-162 °C. Despite the high nitrogen contents, these complexes...

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Snyder CJ, Martin PD, Heeg MJ, et al. Synthesis, structure, and properties of group 1 metal complexes containing nitrogen-rich hydrotris(tetrazolyl)borate ligands. Chemistry. 2013;19(10):3306-10doi: 10.1002/chem.201203990.
Snyder, C. J., Martin, P. D., Heeg, M. J., & Winter, C. H. (2013). Synthesis, structure, and properties of group 1 metal complexes containing nitrogen-rich hydrotris(tetrazolyl)borate ligands. Chemistry (Weinheim an der Bergstrasse, Germany), 19(10), 3306-10. https://doi.org/10.1002/chem.201203990
Snyder, Christopher J, et al. "Synthesis, structure, and properties of group 1 metal complexes containing nitrogen-rich hydrotris(tetrazolyl)borate ligands." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 19,10 (2013): 3306-10. doi: https://doi.org/10.1002/chem.201203990
Snyder CJ, Martin PD, Heeg MJ, Winter CH. Synthesis, structure, and properties of group 1 metal complexes containing nitrogen-rich hydrotris(tetrazolyl)borate ligands. Chemistry. 2013 Mar 04;19(10):3306-10. doi: 10.1002/chem.201203990. Epub 2013 Feb 05. PMID: 23386471.
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Splitting a Substrate into Three Parts: Gold-Catalyzed Nitrogenation of Alkynes by C-C and C≡C Bond Cleavage.

Angewandte Chemie (International ed. in English)

Qin C, Su Y, Shen T, Shi X, Jiao N.
PMID: 26494539
Angew Chem Int Ed Engl. 2016 Jan 04;55(1):350-4. doi: 10.1002/anie.201508347. Epub 2015 Oct 23.

A gold-catalyzed nitrogenation of alkynes for the synthesis of carbamides and amino tetrazoles through C-C and C≡C bond cleavages is described. A diverse set of functionalized carbamide and amino tetrazole derivatives were selectively constructed under mild conditions. The chemoselectivity...

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Qin C, Su Y, Shen T, et al. Splitting a Substrate into Three Parts: Gold-Catalyzed Nitrogenation of Alkynes by C-C and C≡C Bond Cleavage. Angew Chem Int Ed Engl. 2015;55(1):350-4doi: 10.1002/anie.201508347.
Qin, C., Su, Y., Shen, T., Shi, X., & Jiao, N. (2016). Splitting a Substrate into Three Parts: Gold-Catalyzed Nitrogenation of Alkynes by C-C and C≡C Bond Cleavage. Angewandte Chemie (International ed. in English), 55(1), 350-4. https://doi.org/10.1002/anie.201508347
Qin, Chong, et al. "Splitting a Substrate into Three Parts: Gold-Catalyzed Nitrogenation of Alkynes by C-C and C≡C Bond Cleavage." Angewandte Chemie (International ed. in English) vol. 55,1 (2016): 350-4. doi: https://doi.org/10.1002/anie.201508347
Qin C, Su Y, Shen T, Shi X, Jiao N. Splitting a Substrate into Three Parts: Gold-Catalyzed Nitrogenation of Alkynes by C-C and C≡C Bond Cleavage. Angew Chem Int Ed Engl. 2016 Jan 04;55(1):350-4. doi: 10.1002/anie.201508347. Epub 2015 Oct 23. PMID: 26494539.
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Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation.

Organic & biomolecular chemistry

Wang L, Wu W, Chen Q, He M.
PMID: 25209148
Org Biomol Chem. 2014 Oct 28;12(40):7923-6. doi: 10.1039/c4ob01440e. Epub 2014 Sep 11.

Rh(III)-catalyzed direct olefination reaction via aromatic C-H bond activation is described using tetrazole as the directing group. This reaction provides a straightforward way for the synthesis of ortho-alkenyl aryl tetrazoles. Various functional groups tolerate the reaction conditions and afford...

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Wang L, Wu W, Chen Q, et al. Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation. Org Biomol Chem. 2014;12(40):7923-6doi: 10.1039/c4ob01440e.
Wang, L., Wu, W., Chen, Q., & He, M. (2014). Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation. Organic & biomolecular chemistry, 12(40), 7923-6. https://doi.org/10.1039/c4ob01440e
Wang, Liang, et al. "Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation." Organic & biomolecular chemistry vol. 12,40 (2014): 7923-6. doi: https://doi.org/10.1039/c4ob01440e
Wang L, Wu W, Chen Q, He M. Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation. Org Biomol Chem. 2014 Oct 28;12(40):7923-6. doi: 10.1039/c4ob01440e. Epub 2014 Sep 11. PMID: 25209148.
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Showing 1 to 12 of 167 entries