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A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization.

Chemical communications (Cambridge, England)

Li Z, Xiao Y, Liu ZQ.
PMID: 25997410
Chem Commun (Camb). 2015 Jun 21;51(49):9969-71. doi: 10.1039/c5cc02968f.

An efficient hydrocyanoalkylation of unactivated alkenes with alkyl nitriles was developed. Through this free-radical-initiated selective activation of the α-C(sp(3))-H bond of acetonitriles, an anti-Markovnikov addition of an α-cyano C-centered radical to olefins has been achieved, which allows a facile...

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Li Z, Xiao Y, Liu ZQ. A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization. Chem Commun (Camb). 2015;51(49):9969-71doi: 10.1039/c5cc02968f.
Li, Z., Xiao, Y., & Liu, Z. Q. (2015). A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization. Chemical communications (Cambridge, England), 51(49), 9969-71. https://doi.org/10.1039/c5cc02968f
Li, Zejiang, et al. "A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization." Chemical communications (Cambridge, England) vol. 51,49 (2015): 9969-71. doi: https://doi.org/10.1039/c5cc02968f
Li Z, Xiao Y, Liu ZQ. A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization. Chem Commun (Camb). 2015 Jun 21;51(49):9969-71. doi: 10.1039/c5cc02968f. PMID: 25997410.
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Synthesis of 3-Cyano-1H-indoles and Their 2'-Deoxyribonucleoside Derivatives through One-Pot Cascade Reactions.

The Journal of organic chemistry

Li B, Zhang B, Zhang X, Fan X.
PMID: 27513004
J Org Chem. 2016 Oct 21;81(20):9530-9538. doi: 10.1021/acs.joc.6b01612. Epub 2016 Aug 15.

An efficient and economical synthetic approach toward 3-cyano-1H-indoles through the reactions of 2-(2-bromophenyl)acetonitriles with aldehydes and aqueous ammonia is presented. Mechanically, this novel protocol involves a one-pot cascade procedure consisting of an aldol-type condensation, a copper-catalyzed amination by using...

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Li B, Zhang B, Zhang X, et al. Synthesis of 3-Cyano-1H-indoles and Their 2'-Deoxyribonucleoside Derivatives through One-Pot Cascade Reactions. J Org Chem. 2016;81(20):9530-9538doi: 10.1021/acs.joc.6b01612.
Li, B., Zhang, B., Zhang, X., & Fan, X. (2016). Synthesis of 3-Cyano-1H-indoles and Their 2'-Deoxyribonucleoside Derivatives through One-Pot Cascade Reactions. The Journal of organic chemistry, 81(20), 9530-9538. https://doi.org/10.1021/acs.joc.6b01612
Li, Bin, et al. "Synthesis of 3-Cyano-1H-indoles and Their 2'-Deoxyribonucleoside Derivatives through One-Pot Cascade Reactions." The Journal of organic chemistry vol. 81,20 (2016): 9530-9538. doi: https://doi.org/10.1021/acs.joc.6b01612
Li B, Zhang B, Zhang X, Fan X. Synthesis of 3-Cyano-1H-indoles and Their 2'-Deoxyribonucleoside Derivatives through One-Pot Cascade Reactions. J Org Chem. 2016 Oct 21;81(20):9530-9538. doi: 10.1021/acs.joc.6b01612. Epub 2016 Aug 15. PMID: 27513004.
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Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration.

Chemical communications (Cambridge, England)

Li Y, Liu B, Li HB, Wang Q, Li JH.
PMID: 25446150
Chem Commun (Camb). 2015 Jan 21;51(6):1024-6. doi: 10.1039/c4cc08902b.

A novel metal-free oxidative 1,2-alkylarylation of unactivated alkenes with the α-C(sp(3))-H bonds of acetonitriles for the synthesis of 5-oxo-pentanenitriles is presented. In the presence of TBPB (tert-butyl peroxybenzoate), a variety of α-aryl allylic alcohols underwent the 1,2-alkylarylation reaction with...

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Li Y, Liu B, Li HB, et al. Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration. Chem Commun (Camb). 2015;51(6):1024-6doi: 10.1039/c4cc08902b.
Li, Y., Liu, B., Li, H. B., Wang, Q., & Li, J. H. (2015). Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration. Chemical communications (Cambridge, England), 51(6), 1024-6. https://doi.org/10.1039/c4cc08902b
Li, Yang, et al. "Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration." Chemical communications (Cambridge, England) vol. 51,6 (2015): 1024-6. doi: https://doi.org/10.1039/c4cc08902b
Li Y, Liu B, Li HB, Wang Q, Li JH. Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration. Chem Commun (Camb). 2015 Jan 21;51(6):1024-6. doi: 10.1039/c4cc08902b. PMID: 25446150.
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Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones.

Organic letters

Jinzaki T, Arakawa M, Kinoshita H, Ichikawa J, Miura K.
PMID: 23837593
Org Lett. 2013 Jul 19;15(14):3750-3. doi: 10.1021/ol401663u. Epub 2013 Jul 09.

α-Alkylated (dimethylsilyl)acetonitriles (Me2HSiCR(3)R(4)CN) react spontaneously with aldehydes in DMSO to give β-hydroxynitriles in good to high yields. The addition to ketones is effectively promoted by using MgCl2 or CaCl2. (Dimethylsilyl)acetonitrile (Me2HSiCH2CN) shows lower reactivity than the α-alkylated analogues. However,...

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Jinzaki T, Arakawa M, Kinoshita H, et al. Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones. Org Lett. 2013;15(14):3750-3doi: 10.1021/ol401663u.
Jinzaki, T., Arakawa, M., Kinoshita, H., Ichikawa, J., & Miura, K. (2013). Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones. Organic letters, 15(14), 3750-3. https://doi.org/10.1021/ol401663u
Jinzaki, Takaaki, et al. "Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones." Organic letters vol. 15,14 (2013): 3750-3. doi: https://doi.org/10.1021/ol401663u
Jinzaki T, Arakawa M, Kinoshita H, Ichikawa J, Miura K. Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones. Org Lett. 2013 Jul 19;15(14):3750-3. doi: 10.1021/ol401663u. Epub 2013 Jul 09. PMID: 23837593.
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Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation.

Chemical communications (Cambridge, England)

Zhou K, Liu JB, Xie W, Ye S, Wu J.
PMID: 32010913
Chem Commun (Camb). 2020 Feb 27;56(17):2554-2557. doi: 10.1039/d0cc00351d.

Metal-free insertion of sulfur dioxide with aryl iodides and 3-azido-2-methylbut-3-en-2-ol under ultraviolet irradiation at room temperature is achieved, giving rise to 2-(arylsulfonyl)acetonitriles in moderate to good yields. Alkyl iodide is also workable under these conditions. This transformation proceeds smoothly...

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Zhou K, Liu JB, Xie W, et al. Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation. Chem Commun (Camb). 2020;56(17):2554-2557doi: 10.1039/d0cc00351d.
Zhou, K., Liu, J. B., Xie, W., Ye, S., & Wu, J. (2020). Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation. Chemical communications (Cambridge, England), 56(17), 2554-2557. https://doi.org/10.1039/d0cc00351d
Zhou, Kaida, et al. "Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation." Chemical communications (Cambridge, England) vol. 56,17 (2020): 2554-2557. doi: https://doi.org/10.1039/d0cc00351d
Zhou K, Liu JB, Xie W, Ye S, Wu J. Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation. Chem Commun (Camb). 2020 Feb 27;56(17):2554-2557. doi: 10.1039/d0cc00351d. PMID: 32010913.
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A novel approach to bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes .

Organic & biomolecular chemistry

Kutasevich AV, Niktarov AS, Uvarova ES, Karnoukhova VA, Mityanov VS.
PMID: 34596641
Org Biomol Chem. 2021 Oct 27;19(41):8988-8998. doi: 10.1039/d1ob01441b.

A new synthetic approach for obtaining previously unknown bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes has been developed. It is based on 1,3-dipolar cycloaddition between 2-unsubstituted imidazole

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Kutasevich AV, Niktarov AS, Uvarova ES, et al. A novel approach to bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes . Org Biomol Chem. 2021;19(41):8988-8998doi: 10.1039/d1ob01441b.
Kutasevich, A. V., Niktarov, A. S., Uvarova, E. S., Karnoukhova, V. A., & Mityanov, V. S. (2021). A novel approach to bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes . Organic & biomolecular chemistry, 19(41), 8988-8998. https://doi.org/10.1039/d1ob01441b
Kutasevich, Anton V, et al. "A novel approach to bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes ." Organic & biomolecular chemistry vol. 19,41 (2021): 8988-8998. doi: https://doi.org/10.1039/d1ob01441b
Kutasevich AV, Niktarov AS, Uvarova ES, Karnoukhova VA, Mityanov VS. A novel approach to bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes . Org Biomol Chem. 2021 Oct 27;19(41):8988-8998. doi: 10.1039/d1ob01441b. PMID: 34596641.
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Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles.

Organic & biomolecular chemistry

Gong J, Hu K, Shao Y, Li R, Zhang Y, Hu M, Chen J.
PMID: 31850443
Org Biomol Chem. 2020 Jan 22;18(3):488-494. doi: 10.1039/c9ob02408e.

The first example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wide functional group compatibility. Preliminary mechanistic experiments indicate that...

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Gong J, Hu K, Shao Y, et al. Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles. Org Biomol Chem. 2020;18(3):488-494doi: 10.1039/c9ob02408e.
Gong, J., Hu, K., Shao, Y., Li, R., Zhang, Y., Hu, M., & Chen, J. (2020). Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles. Organic & biomolecular chemistry, 18(3), 488-494. https://doi.org/10.1039/c9ob02408e
Gong, Julin, et al. "Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles." Organic & biomolecular chemistry vol. 18,3 (2020): 488-494. doi: https://doi.org/10.1039/c9ob02408e
Gong J, Hu K, Shao Y, Li R, Zhang Y, Hu M, Chen J. Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles. Org Biomol Chem. 2020 Jan 22;18(3):488-494. doi: 10.1039/c9ob02408e. PMID: 31850443.
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Reactions of group 4 metallocenes with monosubstituted acetonitriles: keteniminate formation versus C-C coupling.

Chemistry (Weinheim an der Bergstrasse, Germany)

Becker L, Haehnel M, Spannenberg A, Arndt P, Rosenthal U.
PMID: 25641093
Chemistry. 2015 Feb 16;21(8):3242-8. doi: 10.1002/chem.201406219. Epub 2015 Jan 12.

The reactions of the Group 4 metallocene dichlorides [Cp'2 MCl2 ] (1 a: M=Ti, Cp'=Cp*=η(5) -pentamethylcyclopentadienyl, 1 b: M=Zr, Cp'=Cp=η(5) -cyclopentadienyl) with lithiated MesCH2-C≡N gave [Cp*2 TiCl(N=C=C(HMes))] (3; Mes=mesityl) in the case of 1 a. For compound 1 b,...

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Becker L, Haehnel M, Spannenberg A, et al. Reactions of group 4 metallocenes with monosubstituted acetonitriles: keteniminate formation versus C-C coupling. Chemistry. 2015;21(8):3242-8doi: 10.1002/chem.201406219.
Becker, L., Haehnel, M., Spannenberg, A., Arndt, P., & Rosenthal, U. (2015). Reactions of group 4 metallocenes with monosubstituted acetonitriles: keteniminate formation versus C-C coupling. Chemistry (Weinheim an der Bergstrasse, Germany), 21(8), 3242-8. https://doi.org/10.1002/chem.201406219
Becker, Lisanne, et al. "Reactions of group 4 metallocenes with monosubstituted acetonitriles: keteniminate formation versus C-C coupling." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,8 (2015): 3242-8. doi: https://doi.org/10.1002/chem.201406219
Becker L, Haehnel M, Spannenberg A, Arndt P, Rosenthal U. Reactions of group 4 metallocenes with monosubstituted acetonitriles: keteniminate formation versus C-C coupling. Chemistry. 2015 Feb 16;21(8):3242-8. doi: 10.1002/chem.201406219. Epub 2015 Jan 12. PMID: 25641093.
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Optical resolution of alpha-alkyl phenyl acetonitriles by HPLC on cellulose triacetate chiral stationary phases coated on underivatized silica gel.

Chirality

Chen X, Zou H, Yang L, Wang H, Zhang Q.
PMID: 10897099
Chirality. 2000 Aug;12(8):621-6. doi: 10.1002/1520-636X(2000)12:8<621::AID-CHIR4>3.0.CO;2-A.

Microcrystalline celluloses from two sources were used to prepare cellulose triacetate chiral stationary phases (CSPs) coated on underivatized silica gel, which shows discriminating chiral recognition for enantiomers. The chiral separation of four alpha-alkyl phenyl acetonitriles was investigated on the...

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Chen X, Zou H, Yang L, et al. Optical resolution of alpha-alkyl phenyl acetonitriles by HPLC on cellulose triacetate chiral stationary phases coated on underivatized silica gel. Chirality. 2000;12(8):621-6doi: 10.1002/1520-636X(2000)12:8<621::AID-CHIR4>3.0.CO;2-A.
Chen, X., Zou, H., Yang, L., Wang, H., & Zhang, Q. (2000). Optical resolution of alpha-alkyl phenyl acetonitriles by HPLC on cellulose triacetate chiral stationary phases coated on underivatized silica gel. Chirality, 12(8), 621-6. https://doi.org/10.1002/1520-636X(2000)12:8<621::AID-CHIR4>3.0.CO;2-A
Chen, et al. "Optical resolution of alpha-alkyl phenyl acetonitriles by HPLC on cellulose triacetate chiral stationary phases coated on underivatized silica gel." Chirality vol. 12,8 (2000): 621-6. doi: https://doi.org/10.1002/1520-636X(2000)12:8<621::AID-CHIR4>3.0.CO;2-A
Chen X, Zou H, Yang L, Wang H, Zhang Q. Optical resolution of alpha-alkyl phenyl acetonitriles by HPLC on cellulose triacetate chiral stationary phases coated on underivatized silica gel. Chirality. 2000 Aug;12(8):621-6. doi: 10.1002/1520-636X(2000)12:8<621::AID-CHIR4>3.0.CO;2-A. PMID: 10897099.
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Stereoselective synthesis of 2-alkylidene-3-iminoindoles by reaction of 1,1-dianions with oxalic acid bis(imidoyl) chlorides.

The Journal of organic chemistry

Langer P, Wuckelt J, Doring M, Gorls H.
PMID: 10864742
J Org Chem. 2000 Jun 16;65(12):3603-11. doi: 10.1021/jo991701l.

Treatment of dilithiated nitriles and sulfones with oxalic acid bis(imidoyl) chlorides resulted in a new cyclization reaction which provided a variety of (3-imino-2, 3-dihydro-1H-indol-2-ylidene)acetonitriles and -sulfones in good yields. The reactions proceeded by condensation of the dianions with the...

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Langer P, Wuckelt J, Doring M, et al. Stereoselective synthesis of 2-alkylidene-3-iminoindoles by reaction of 1,1-dianions with oxalic acid bis(imidoyl) chlorides. J Org Chem. 2000;65(12):3603-11doi: 10.1021/jo991701l.
Langer, P., Wuckelt, J., Doring, M., & Gorls, H. (2000). Stereoselective synthesis of 2-alkylidene-3-iminoindoles by reaction of 1,1-dianions with oxalic acid bis(imidoyl) chlorides. The Journal of organic chemistry, 65(12), 3603-11. https://doi.org/10.1021/jo991701l
Langer, et al. "Stereoselective synthesis of 2-alkylidene-3-iminoindoles by reaction of 1,1-dianions with oxalic acid bis(imidoyl) chlorides." The Journal of organic chemistry vol. 65,12 (2000): 3603-11. doi: https://doi.org/10.1021/jo991701l
Langer P, Wuckelt J, Doring M, Gorls H. Stereoselective synthesis of 2-alkylidene-3-iminoindoles by reaction of 1,1-dianions with oxalic acid bis(imidoyl) chlorides. J Org Chem. 2000 Jun 16;65(12):3603-11. doi: 10.1021/jo991701l. PMID: 10864742.
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Automated parameterization of quantum-mechanically derived force-fields including explicit sigma holes: A pathway to energetic and structural features of halogen bonds in gas and condensed phase.

The Journal of chemical physics

Campetella M, De Mitri N, Prampolini G.
PMID: 32752684
J Chem Phys. 2020 Jul 28;153(4):044106. doi: 10.1063/5.0014280.

In classical molecular dynamics, general purpose atomistic force-fields (FFs) often deliver inaccurate results when dealing with halogen bonds (XBs), notwithstanding their crucial role in many fields of science, ranging from material design to drug development. Given the large dimensions...

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Campetella M, De Mitri N, Prampolini G. Automated parameterization of quantum-mechanically derived force-fields including explicit sigma holes: A pathway to energetic and structural features of halogen bonds in gas and condensed phase. J Chem Phys. 2020;153(4):044106doi: 10.1063/5.0014280.
Campetella, M., De Mitri, N., & Prampolini, G. (2020). Automated parameterization of quantum-mechanically derived force-fields including explicit sigma holes: A pathway to energetic and structural features of halogen bonds in gas and condensed phase. The Journal of chemical physics, 153(4), 044106. https://doi.org/10.1063/5.0014280
Campetella, Marco, et al. "Automated parameterization of quantum-mechanically derived force-fields including explicit sigma holes: A pathway to energetic and structural features of halogen bonds in gas and condensed phase." The Journal of chemical physics vol. 153,4 (2020): 044106. doi: https://doi.org/10.1063/5.0014280
Campetella M, De Mitri N, Prampolini G. Automated parameterization of quantum-mechanically derived force-fields including explicit sigma holes: A pathway to energetic and structural features of halogen bonds in gas and condensed phase. J Chem Phys. 2020 Jul 28;153(4):044106. doi: 10.1063/5.0014280. PMID: 32752684.
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Synthesis of Thieno-Fused Five- and Six-Membered Nitrogen and Oxygen Heterocycles via Intramolecular Heteroannulation of 4,5-Substituted 3-Amino or 3-Hydroxy 2-Functionalized Thiophenes.

The Journal of organic chemistry

Acharya A, Gautam V, Ila H.
PMID: 28686036
J Org Chem. 2017 Aug 04;82(15):7920-7938. doi: 10.1021/acs.joc.7b01153. Epub 2017 Jul 18.

Diverse general high-yield routes for novel thieno-fused five- and six-membered nitrogen and oxygen heterocycles such as thieno[3,2-b]pyrroles, thieno[3,2-b]furans, thieno[3,2-b]indoles, thieno[3,2-b]benzofurans, thieno[3,2-b]pyridine-5-ones, thieno[3,2-b]pyran-5-ones, thieno[3,2-b]isoquinolin-5-ones, thieno[3,2-b]chromen-5-ones, thieno[3,2-b]quinolin-9-ones, and thieno[3,2-b]chromen-9-ones have been developed via in situ or stepwise intramolecular heteroannulation of newly...

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Acharya A, Gautam V, Ila H. Synthesis of Thieno-Fused Five- and Six-Membered Nitrogen and Oxygen Heterocycles via Intramolecular Heteroannulation of 4,5-Substituted 3-Amino or 3-Hydroxy 2-Functionalized Thiophenes. J Org Chem. 2017;82(15):7920-7938doi: 10.1021/acs.joc.7b01153.
Acharya, A., Gautam, V., & Ila, H. (2017). Synthesis of Thieno-Fused Five- and Six-Membered Nitrogen and Oxygen Heterocycles via Intramolecular Heteroannulation of 4,5-Substituted 3-Amino or 3-Hydroxy 2-Functionalized Thiophenes. The Journal of organic chemistry, 82(15), 7920-7938. https://doi.org/10.1021/acs.joc.7b01153
Acharya, Anand, et al. "Synthesis of Thieno-Fused Five- and Six-Membered Nitrogen and Oxygen Heterocycles via Intramolecular Heteroannulation of 4,5-Substituted 3-Amino or 3-Hydroxy 2-Functionalized Thiophenes." The Journal of organic chemistry vol. 82,15 (2017): 7920-7938. doi: https://doi.org/10.1021/acs.joc.7b01153
Acharya A, Gautam V, Ila H. Synthesis of Thieno-Fused Five- and Six-Membered Nitrogen and Oxygen Heterocycles via Intramolecular Heteroannulation of 4,5-Substituted 3-Amino or 3-Hydroxy 2-Functionalized Thiophenes. J Org Chem. 2017 Aug 04;82(15):7920-7938. doi: 10.1021/acs.joc.7b01153. Epub 2017 Jul 18. PMID: 28686036.
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Showing 1 to 12 of 45 entries