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Steering Asymmetric Lewis Acid Catalysis Exclusively with Octahedral Metal-Centered Chirality.

Accounts of chemical research

Zhang L, Meggers E.
PMID: 28128920
Acc Chem Res. 2017 Feb 21;50(2):320-330. doi: 10.1021/acs.accounts.6b00586. Epub 2017 Jan 27.

Catalysts for asymmetric synthesis must be chiral. Metal-based asymmetric catalysts are typically constructed by assembling chiral ligands around a central metal. In this Account, a new class of effective chiral Lewis acid catalysts is introduced in which the octahedral...

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Zhang L, Meggers E. Steering Asymmetric Lewis Acid Catalysis Exclusively with Octahedral Metal-Centered Chirality. Acc Chem Res. 2017;50(2):320-330doi: 10.1021/acs.accounts.6b00586.
Zhang, L., & Meggers, E. (2017). Steering Asymmetric Lewis Acid Catalysis Exclusively with Octahedral Metal-Centered Chirality. Accounts of chemical research, 50(2), 320-330. https://doi.org/10.1021/acs.accounts.6b00586
Zhang, Lilu, and Meggers, Eric. "Steering Asymmetric Lewis Acid Catalysis Exclusively with Octahedral Metal-Centered Chirality." Accounts of chemical research vol. 50,2 (2017): 320-330. doi: https://doi.org/10.1021/acs.accounts.6b00586
Zhang L, Meggers E. Steering Asymmetric Lewis Acid Catalysis Exclusively with Octahedral Metal-Centered Chirality. Acc Chem Res. 2017 Feb 21;50(2):320-330. doi: 10.1021/acs.accounts.6b00586. Epub 2017 Jan 27. PMID: 28128920.
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The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons.

The Journal of organic chemistry

Yu S, Qi L, Hu K, Gong J, Cheng T, Wang Q, Chen J, Wu H.
PMID: 28288278
J Org Chem. 2017 Apr 07;82(7):3631-3638. doi: 10.1021/acs.joc.7b00148. Epub 2017 Mar 17.

A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the...

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Yu S, Qi L, Hu K, et al. The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons. J Org Chem. 2017;82(7):3631-3638doi: 10.1021/acs.joc.7b00148.
Yu, S., Qi, L., Hu, K., Gong, J., Cheng, T., Wang, Q., Chen, J., & Wu, H. (2017). The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons. The Journal of organic chemistry, 82(7), 3631-3638. https://doi.org/10.1021/acs.joc.7b00148
Yu, Shuling, et al. "The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons." The Journal of organic chemistry vol. 82,7 (2017): 3631-3638. doi: https://doi.org/10.1021/acs.joc.7b00148
Yu S, Qi L, Hu K, Gong J, Cheng T, Wang Q, Chen J, Wu H. The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons. J Org Chem. 2017 Apr 07;82(7):3631-3638. doi: 10.1021/acs.joc.7b00148. Epub 2017 Mar 17. PMID: 28288278.
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Formylnitroenamines: useful building blocks for nitrated pyridones and aminopyridines with functional groups.

Organic & biomolecular chemistry

Nakaike Y, Hayashi D, Nishiwaki N, Tobe Y, Ariga M.
PMID: 19109678
Org Biomol Chem. 2009 Jan 21;7(2):325-34. doi: 10.1039/b815306j. Epub 2008 Nov 17.

beta-formyl-beta-nitroenamines possess both an electrophilic formyl group and a nucleophilic amino group and, therefore, serve as C3N1 building blocks having a nitro group to afford nitropyridones and aminonitropyridines with a functional group at the 3-position. Upon treatment with malonic...

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Nakaike Y, Hayashi D, Nishiwaki N, et al. Formylnitroenamines: useful building blocks for nitrated pyridones and aminopyridines with functional groups. Org Biomol Chem. 2008;7(2):325-34doi: 10.1039/b815306j.
Nakaike, Y., Hayashi, D., Nishiwaki, N., Tobe, Y., & Ariga, M. (2009). Formylnitroenamines: useful building blocks for nitrated pyridones and aminopyridines with functional groups. Organic & biomolecular chemistry, 7(2), 325-34. https://doi.org/10.1039/b815306j
Nakaike, Yumi, et al. "Formylnitroenamines: useful building blocks for nitrated pyridones and aminopyridines with functional groups." Organic & biomolecular chemistry vol. 7,2 (2009): 325-34. doi: https://doi.org/10.1039/b815306j
Nakaike Y, Hayashi D, Nishiwaki N, Tobe Y, Ariga M. Formylnitroenamines: useful building blocks for nitrated pyridones and aminopyridines with functional groups. Org Biomol Chem. 2009 Jan 21;7(2):325-34. doi: 10.1039/b815306j. Epub 2008 Nov 17. PMID: 19109678.
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Asymmetric Photocatalysis with Bis-cyclometalated Rhodium Complexes.

Accounts of chemical research

Huang X, Meggers E.
PMID: 30840435
Acc Chem Res. 2019 Mar 19;52(3):833-847. doi: 10.1021/acs.accounts.9b00028. Epub 2019 Mar 06.

Aspects of sustainability are playing an increasingly important role for the development of new synthetic methods. In this context, the combination of asymmetric catalysis, which is considered one of the most economic strategies to generate nonracemic chiral compounds, and...

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Huang X, Meggers E. Asymmetric Photocatalysis with Bis-cyclometalated Rhodium Complexes. Acc Chem Res. 2019;52(3):833-847doi: 10.1021/acs.accounts.9b00028.
Huang, X., & Meggers, E. (2019). Asymmetric Photocatalysis with Bis-cyclometalated Rhodium Complexes. Accounts of chemical research, 52(3), 833-847. https://doi.org/10.1021/acs.accounts.9b00028
Huang, Xiaoqiang, and Meggers, Eric. "Asymmetric Photocatalysis with Bis-cyclometalated Rhodium Complexes." Accounts of chemical research vol. 52,3 (2019): 833-847. doi: https://doi.org/10.1021/acs.accounts.9b00028
Huang X, Meggers E. Asymmetric Photocatalysis with Bis-cyclometalated Rhodium Complexes. Acc Chem Res. 2019 Mar 19;52(3):833-847. doi: 10.1021/acs.accounts.9b00028. Epub 2019 Mar 06. PMID: 30840435.
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Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2-(2-Alkynylphenyl)acetonitriles and Alkynones.

The Journal of organic chemistry

Chen LL, Zhang JW, Yang WW, Fu JY, Zhu JY, Wang YB.
PMID: 31140272
J Org Chem. 2019 Jun 21;84(12):8090-8099. doi: 10.1021/acs.joc.9b00948. Epub 2019 Jun 11.

Effective transition-metal-free formal [4+2] benzannulation for the preparation of 1-cyano-3-acylnaphthalenes from 2-(2-alkynylphenyl)acetonitriles and alkynones through sequential C-C bond coupling has been developed. This protocol is characterized by mild conditions, excellent functional group tolerance, complete regioselectivity, and atom economy. The...

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Chen LL, Zhang JW, Yang WW, et al. Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2-(2-Alkynylphenyl)acetonitriles and Alkynones. J Org Chem. 2019;84(12):8090-8099doi: 10.1021/acs.joc.9b00948.
Chen, L. L., Zhang, J. W., Yang, W. W., Fu, J. Y., Zhu, J. Y., & Wang, Y. B. (2019). Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2-(2-Alkynylphenyl)acetonitriles and Alkynones. The Journal of organic chemistry, 84(12), 8090-8099. https://doi.org/10.1021/acs.joc.9b00948
Chen, Lu-Lu, et al. "Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2-(2-Alkynylphenyl)acetonitriles and Alkynones." The Journal of organic chemistry vol. 84,12 (2019): 8090-8099. doi: https://doi.org/10.1021/acs.joc.9b00948
Chen LL, Zhang JW, Yang WW, Fu JY, Zhu JY, Wang YB. Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2-(2-Alkynylphenyl)acetonitriles and Alkynones. J Org Chem. 2019 Jun 21;84(12):8090-8099. doi: 10.1021/acs.joc.9b00948. Epub 2019 Jun 11. PMID: 31140272.
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One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate.

ACS omega

Saraiah B, Gautam V, Acharya A, Pasha MA, Ila H.
PMID: 31458967
ACS Omega. 2018 Jul 26;3(7):8355-8364. doi: 10.1021/acsomega.8b01172. eCollection 2018 Jul 31.

A one-pot synthesis of 2-(het)aryl/alkyl-3-cyanobenzofurans has been reported. The overall sequence involves base-induced reaction of 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles with benzyl carbamate, generating α-(het)aroyl-α-(2-bromoaryl)acetonitriles, which are in situ subjected to copper-catalyzed intramolecular

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Saraiah B, Gautam V, Acharya A, et al. One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate. ACS Omega. 2018;3(7):8355-8364doi: 10.1021/acsomega.8b01172.
Saraiah, B., Gautam, V., Acharya, A., Pasha, M. A., & Ila, H. (2018). One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate. ACS omega, 3(7), 8355-8364. https://doi.org/10.1021/acsomega.8b01172
Saraiah, Bonagiri, et al. "One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate." ACS omega vol. 3,7 (2018): 8355-8364. doi: https://doi.org/10.1021/acsomega.8b01172
Saraiah B, Gautam V, Acharya A, Pasha MA, Ila H. One-Pot Synthesis of 2-(Het)aryl/alkyl-3-cyanobenzofurans from 2-(2-Bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles and Benzyl Carbamate. ACS Omega. 2018 Jul 26;3(7):8355-8364. doi: 10.1021/acsomega.8b01172. eCollection 2018 Jul 31. PMID: 31458967; PMCID: PMC6644376.
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Synthesis of α-substituted indolylacetamide using acetonitriles as acetamide enolate equivalents through O-transfer reactions.

Chemical communications (Cambridge, England)

Abe T, Noda K, Sawada D.
PMID: 34212954
Chem Commun (Camb). 2021 Jul 29;57(61):7493-7496. doi: 10.1039/d1cc02821a.

We introduce readily available ammonium hemiaminals as O-transfer reagents and commercially available acetonitriles as a primary amide enolate precursor. The combination serves as an amide enolate equivalent, thereby providing one-pot access to α-substituted indolylacetamides. A broad substrate scope and...

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Abe T, Noda K, Sawada D. Synthesis of α-substituted indolylacetamide using acetonitriles as acetamide enolate equivalents through O-transfer reactions. Chem Commun (Camb). 2021;57(61):7493-7496doi: 10.1039/d1cc02821a.
Abe, T., Noda, K., & Sawada, D. (2021). Synthesis of α-substituted indolylacetamide using acetonitriles as acetamide enolate equivalents through O-transfer reactions. Chemical communications (Cambridge, England), 57(61), 7493-7496. https://doi.org/10.1039/d1cc02821a
Abe, Takumi, et al. "Synthesis of α-substituted indolylacetamide using acetonitriles as acetamide enolate equivalents through O-transfer reactions." Chemical communications (Cambridge, England) vol. 57,61 (2021): 7493-7496. doi: https://doi.org/10.1039/d1cc02821a
Abe T, Noda K, Sawada D. Synthesis of α-substituted indolylacetamide using acetonitriles as acetamide enolate equivalents through O-transfer reactions. Chem Commun (Camb). 2021 Jul 29;57(61):7493-7496. doi: 10.1039/d1cc02821a. PMID: 34212954.
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Synthesis and in vitro antiproliferative activity of certain novel pyrazolo[3,4-b]pyridines with potential p38α MAPK-inhibitory activity.

Archiv der Pharmazie

Farahat AA, Samir EM, Zaki MY, Serya RAT, Abdel-Aziz HA.
PMID: 34796536
Arch Pharm (Weinheim). 2021 Nov 18;e2100302. doi: 10.1002/ardp.202100302. Epub 2021 Nov 18.

Novel series of pyrazolo[3,4-b]pyridines 9a-j and 14a-f were prepared via a one-pot three-component reaction. Compounds 9a-j were synthesized by the reaction of 3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-amine (4) with benzoyl acetonitriles 3a,b and aldehydes 5a-e, whereas the spiro derivatives 14a-f were synthesized by...

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Farahat AA, Samir EM, Zaki MY, et al. Synthesis and in vitro antiproliferative activity of certain novel pyrazolo[3,4-b]pyridines with potential p38α MAPK-inhibitory activity. Arch Pharm (Weinheim). 2021;e2100302doi: 10.1002/ardp.202100302.
Farahat, A. A., Samir, E. M., Zaki, M. Y., Serya, R. A. T., & Abdel-Aziz, H. A. (2021). Synthesis and in vitro antiproliferative activity of certain novel pyrazolo[3,4-b]pyridines with potential p38α MAPK-inhibitory activity. Archiv der Pharmazie, e2100302. https://doi.org/10.1002/ardp.202100302
Farahat, Aya A, et al. "Synthesis and in vitro antiproliferative activity of certain novel pyrazolo[3,4-b]pyridines with potential p38α MAPK-inhibitory activity." Archiv der Pharmazie vol. (2021): e2100302. doi: https://doi.org/10.1002/ardp.202100302
Farahat AA, Samir EM, Zaki MY, Serya RAT, Abdel-Aziz HA. Synthesis and in vitro antiproliferative activity of certain novel pyrazolo[3,4-b]pyridines with potential p38α MAPK-inhibitory activity. Arch Pharm (Weinheim). 2021 Nov 18;e2100302. doi: 10.1002/ardp.202100302. Epub 2021 Nov 18. PMID: 34796536.
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Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-.

The Journal of organic chemistry

Aksenov AV, Aleksandrova EV, Aksenov DA, Aksenova AA, Aksenov NA, Nobi MA, Rubin M.
PMID: 34990543
J Org Chem. 2022 Jan 06; doi: 10.1021/acs.joc.1c02753. Epub 2022 Jan 06.

Base-assisted transformations of 2-(3-oxoindolin-2-yl)acetonitriles were investigated. Unexpectedly, attempted reactions of substrates possessing nonprotected nitrogen atoms were accompanied by unusual extrusions of 2-arylacetonitriles, followed by a 1,2-aryl shift to afford 3-hydroxyindolin-2-ones. On the other hand, the reactions for

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Aksenov AV, Aleksandrova EV, Aksenov DA, et al. Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-. J Org Chem. 2022;doi: 10.1021/acs.joc.1c02753.
Aksenov, A. V., Aleksandrova, E. V., Aksenov, D. A., Aksenova, A. A., Aksenov, N. A., Nobi, M. A., & Rubin, M. (2022). Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-. The Journal of organic chemistry, . https://doi.org/10.1021/acs.joc.1c02753
Aksenov, Alexander V, et al. "Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-." The Journal of organic chemistry vol. (2022). doi: https://doi.org/10.1021/acs.joc.1c02753
Aksenov AV, Aleksandrova EV, Aksenov DA, Aksenova AA, Aksenov NA, Nobi MA, Rubin M. Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-. J Org Chem. 2022 Jan 06; doi: 10.1021/acs.joc.1c02753. Epub 2022 Jan 06. PMID: 34990543.
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Facile Routes to Manganese(II) Triflate Complexes.

Inorganic chemistry communications

Riedel PJ, Arulsamy N, Mehn MP.
PMID: 21660114
Inorg Chem Commun. 2011 May;14(5):734-737. doi: 10.1016/j.inoche.2011.02.022.

Manganese(II) chloride reacts with trimethylsilyl triflate (TMS(OTf) where OTf = (-)OSO(2)CF(3)) in a 1:1 mixture of acetonitrile and tetrahydrofuran, and after recrystallization affords the linear coordination polymer [Mn(II)(CH(3)CN)(2)(OTf)(2)](n). Each distorted octahedral manganese(II) center in the polymeric chain has trans-acetonitriles...

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Riedel PJ, Arulsamy N, Mehn MP. Facile Routes to Manganese(II) Triflate Complexes. Inorg Chem Commun. 2011;14(5):734-737doi: 10.1016/j.inoche.2011.02.022.
Riedel, P. J., Arulsamy, N., & Mehn, M. P. (2011). Facile Routes to Manganese(II) Triflate Complexes. Inorganic chemistry communications, 14(5), 734-737. https://doi.org/10.1016/j.inoche.2011.02.022
Riedel, Paul J, et al. "Facile Routes to Manganese(II) Triflate Complexes." Inorganic chemistry communications vol. 14,5 (2011): 734-737. doi: https://doi.org/10.1016/j.inoche.2011.02.022
Riedel PJ, Arulsamy N, Mehn MP. Facile Routes to Manganese(II) Triflate Complexes. Inorg Chem Commun. 2011 May;14(5):734-737. doi: 10.1016/j.inoche.2011.02.022. PMID: 21660114; PMCID: PMC3108847.
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An unexpected three-component condensation leading to amino- (3-oxo-2,3-dihydro-1H-isoindol-1-ylidene)- acetonitriles.

The Journal of organic chemistry

Opatz T, Ferenc D.
PMID: 15549828
J Org Chem. 2004 Nov 26;69(24):8496-9. doi: 10.1021/jo0486802.

The reaction of 2-carboxybenzaldehyde with primary amines in the presence of cyanide leads to the formation of 2-substituted amino(3-oxo-2,3-dihydro-1H-isoindol-1-ylidene)acetonitriles. These compounds originate from the condensation of 2-carboxybenzaldehyde with the amine and two molecules of hydrogen cyanide and represent a...

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Opatz T, Ferenc D. An unexpected three-component condensation leading to amino- (3-oxo-2,3-dihydro-1H-isoindol-1-ylidene)- acetonitriles. J Org Chem. 2004;69(24):8496-9doi: 10.1021/jo0486802.
Opatz, T., & Ferenc, D. (2004). An unexpected three-component condensation leading to amino- (3-oxo-2,3-dihydro-1H-isoindol-1-ylidene)- acetonitriles. The Journal of organic chemistry, 69(24), 8496-9. https://doi.org/10.1021/jo0486802
Opatz, Till, and Ferenc, Dorota. "An unexpected three-component condensation leading to amino- (3-oxo-2,3-dihydro-1H-isoindol-1-ylidene)- acetonitriles." The Journal of organic chemistry vol. 69,24 (2004): 8496-9. doi: https://doi.org/10.1021/jo0486802
Opatz T, Ferenc D. An unexpected three-component condensation leading to amino- (3-oxo-2,3-dihydro-1H-isoindol-1-ylidene)- acetonitriles. J Org Chem. 2004 Nov 26;69(24):8496-9. doi: 10.1021/jo0486802. PMID: 15549828.
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Self-assembly of a mixed-ligand silver-based coordination polymer.

Acta crystallographica. Section C, Crystal structure communications

Feazell RP, Carson CE, Klausmeyer KK.
PMID: 15528816
Acta Crystallogr C. 2004 Nov;60:m598-600. doi: 10.1107/S0108270104025004. Epub 2004 Oct 31.

The novel title silver(I) coordination polymer, catena-poly[[acetonitrilesilver(I)]-di-mu-4-[N-(diphenylphosphino)aminomethyl]pyridine-kappa(2)N(1):P;kappa(2)P:N(1)-[acetonitrilesilver(I)]-mu(3)-4-[N,N-bis(diphenylphosphino)aminomethyl]pyridine-kappa(3)N(1):P:P'-bis[acetonitrilesilver(I)(Ag-Ag)]-mu(3)-4-[N,N-bis(diphenylphosphino)aminomethyl]pyridine-kappa(3)P:P':N(1)] tetrakis(tetrafluoroborate) acetonitrile trisolvate], [[Ag(4)(C(2)H(3)N)(4)(C(18)H(17)N(2)P)(2)(C(30)H(26)N(2)P(2))(2)](BF(4))(4).3C(2)H(3)N](n), is formed by the self-assembly of the Ph(2)P(4-NHCH(2)C(5)H(4)N) and (Ph(2)P)(2)(4-NCH(2)C(5)H(4)N) ligands with silver tetrafluoroborate. The polymer consists of alternating rings (which lie about inversion centers) bridged by the...

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Feazell RP, Carson CE, Klausmeyer KK. Self-assembly of a mixed-ligand silver-based coordination polymer. Acta Crystallogr C. 2004;60:m598-600doi: 10.1107/S0108270104025004.
Feazell, R. P., Carson, C. E., & Klausmeyer, K. K. (2004). Self-assembly of a mixed-ligand silver-based coordination polymer. Acta crystallographica. Section C, Crystal structure communications, 60m598-600. https://doi.org/10.1107/S0108270104025004
Feazell, Rodney P, et al. "Self-assembly of a mixed-ligand silver-based coordination polymer." Acta crystallographica. Section C, Crystal structure communications vol. 60 (2004): m598-600. doi: https://doi.org/10.1107/S0108270104025004
Feazell RP, Carson CE, Klausmeyer KK. Self-assembly of a mixed-ligand silver-based coordination polymer. Acta Crystallogr C. 2004 Nov;60:m598-600. doi: 10.1107/S0108270104025004. Epub 2004 Oct 31. PMID: 15528816.
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