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Role of axial donors in the ligand isomerization processes of quadruply bonded dimolybdenum(II) compounds.

Inorganic chemistry

Majumdar M, Patra SK, Kannan M, Dunbar KR, Bera JK.
PMID: 18269221
Inorg Chem. 2008 Mar 17;47(6):2212-22. doi: 10.1021/ic702298v. Epub 2008 Feb 12.

Quadruply bonded dimolybdenum(II) complexes with NP-R (2-(2-R)-1,8-naphthyridine; R = thiazolyl (NP-tz), furyl (NP-fu), thienyl (NP-th)) and 2,3-dimethyl-1,8-naphthyridine (NP-Me 2) have been synthesized by reactions of cis-[Mo2(OAc)2(CH3CN)6][BF4]2 with the corresponding ligands. The products cis-[Mo2(NP-tz)2(OAc)2][BF4]2 (1), trans-[Mo2(NP-fu)2(OAc)2][BF4]2 (2), trans-[Mo2(NP-th)2(OAc)2][BF4]2 (3), and...

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Majumdar M, Patra SK, Kannan M, et al. Role of axial donors in the ligand isomerization processes of quadruply bonded dimolybdenum(II) compounds. Inorg Chem. 2008;47(6):2212-22doi: 10.1021/ic702298v.
Majumdar, M., Patra, S. K., Kannan, M., Dunbar, K. R., & Bera, J. K. (2008). Role of axial donors in the ligand isomerization processes of quadruply bonded dimolybdenum(II) compounds. Inorganic chemistry, 47(6), 2212-22. https://doi.org/10.1021/ic702298v
Majumdar, Moumita, et al. "Role of axial donors in the ligand isomerization processes of quadruply bonded dimolybdenum(II) compounds." Inorganic chemistry vol. 47,6 (2008): 2212-22. doi: https://doi.org/10.1021/ic702298v
Majumdar M, Patra SK, Kannan M, Dunbar KR, Bera JK. Role of axial donors in the ligand isomerization processes of quadruply bonded dimolybdenum(II) compounds. Inorg Chem. 2008 Mar 17;47(6):2212-22. doi: 10.1021/ic702298v. Epub 2008 Feb 12. PMID: 18269221.
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Catalytic α-monoallylation of aryl acetonitriles.

Organic letters

Maji T, Tunge JA.
PMID: 25238334
Org Lett. 2014 Oct 03;16(19):5072-5. doi: 10.1021/ol5024294. Epub 2014 Sep 19.

α-Cyano aldehydes undergo selective transition-metal-catalyzed monoallylation to provide α-allylated nitriles. The transformation leads to linear substitution products with palladium catalysts or branched allylated nitriles using an iridium catalyst. Facile TBD-catalyzed retro-Claisen cleavage is leveraged to attain selective monoallylation.

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Maji T, Tunge JA. Catalytic α-monoallylation of aryl acetonitriles. Org Lett. 2014;16(19):5072-5doi: 10.1021/ol5024294.
Maji, T., & Tunge, J. A. (2014). Catalytic α-monoallylation of aryl acetonitriles. Organic letters, 16(19), 5072-5. https://doi.org/10.1021/ol5024294
Maji, Tapan, and Tunge, Jon A. "Catalytic α-monoallylation of aryl acetonitriles." Organic letters vol. 16,19 (2014): 5072-5. doi: https://doi.org/10.1021/ol5024294
Maji T, Tunge JA. Catalytic α-monoallylation of aryl acetonitriles. Org Lett. 2014 Oct 03;16(19):5072-5. doi: 10.1021/ol5024294. Epub 2014 Sep 19. PMID: 25238334.
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Expedited Route to Fully Substituted Amino-Pyrazole Building Blocks and Their Further Transformations.

ACS omega

Kuleshova O, Khilya O, Volovenko Y, Mallet-Ladeira S, Dyakonenko V, Gras E.
PMID: 31457419
ACS Omega. 2017 Dec 13;2(12):8911-8927. doi: 10.1021/acsomega.7b01419. eCollection 2017 Dec 31.

We report here an efficient and easily reproducible two-step approach to heterocycle-substituted amino-pyrazoles from heterocyclic acetonitriles and their unprecedented subsequent transformations to fully substituted pyrazoles. Such transformations include regioselective derivatization from polyamino derivatives, formation of tetracyclic compounds in up...

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Kuleshova O, Khilya O, Volovenko Y, et al. Expedited Route to Fully Substituted Amino-Pyrazole Building Blocks and Their Further Transformations. ACS Omega. 2017;2(12):8911-8927doi: 10.1021/acsomega.7b01419.
Kuleshova, O., Khilya, O., Volovenko, Y., Mallet-Ladeira, S., Dyakonenko, V., & Gras, E. (2017). Expedited Route to Fully Substituted Amino-Pyrazole Building Blocks and Their Further Transformations. ACS omega, 2(12), 8911-8927. https://doi.org/10.1021/acsomega.7b01419
Kuleshova, Olena, et al. "Expedited Route to Fully Substituted Amino-Pyrazole Building Blocks and Their Further Transformations." ACS omega vol. 2,12 (2017): 8911-8927. doi: https://doi.org/10.1021/acsomega.7b01419
Kuleshova O, Khilya O, Volovenko Y, Mallet-Ladeira S, Dyakonenko V, Gras E. Expedited Route to Fully Substituted Amino-Pyrazole Building Blocks and Their Further Transformations. ACS Omega. 2017 Dec 13;2(12):8911-8927. doi: 10.1021/acsomega.7b01419. eCollection 2017 Dec 31. PMID: 31457419; PMCID: PMC6645537.
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A base-mediated aerobic oxidative synthesis of cyclopent-2-enol derivatives from doubly activated cyclopropanes and substituted acetonitriles.

Organic & biomolecular chemistry

Han XD, Peng GL, Xiong W, Gan R, Fu JP, Wu L, Tang ZS, Hu JW, Wang HB.
PMID: 35019920
Org Biomol Chem. 2022 Jan 12; doi: 10.1039/d1ob02155a. Epub 2022 Jan 12.

We report here that polysubstituted cyclopent-2-enols can be constructed by the one-pot reaction of doubly activated cyclopropanes and α-EWG substituted acetonitriles under mild basic conditions

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Han XD, Peng GL, Xiong W, et al. A base-mediated aerobic oxidative synthesis of cyclopent-2-enol derivatives from doubly activated cyclopropanes and substituted acetonitriles. Org Biomol Chem. 2022;doi: 10.1039/d1ob02155a.
Han, X. D., Peng, G. L., Xiong, W., Gan, R., Fu, J. P., Wu, L., Tang, Z. S., Hu, J. W., & Wang, H. B. (2022). A base-mediated aerobic oxidative synthesis of cyclopent-2-enol derivatives from doubly activated cyclopropanes and substituted acetonitriles. Organic & biomolecular chemistry, . https://doi.org/10.1039/d1ob02155a
Han, Xiao-Dan, et al. "A base-mediated aerobic oxidative synthesis of cyclopent-2-enol derivatives from doubly activated cyclopropanes and substituted acetonitriles." Organic & biomolecular chemistry vol. (2022). doi: https://doi.org/10.1039/d1ob02155a
Han XD, Peng GL, Xiong W, Gan R, Fu JP, Wu L, Tang ZS, Hu JW, Wang HB. A base-mediated aerobic oxidative synthesis of cyclopent-2-enol derivatives from doubly activated cyclopropanes and substituted acetonitriles. Org Biomol Chem. 2022 Jan 12; doi: 10.1039/d1ob02155a. Epub 2022 Jan 12. PMID: 35019920.
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Domino carbocationic cyclization of functionalized cyclopropyl ketones: facile one-pot access to peri- and angularly fused polycyclic aromatic and heteroaromatic frameworks.

The Journal of organic chemistry

Nandi S, Kumar UK, Ila H, Junjappa H.
PMID: 12098306
J Org Chem. 2002 Jul 12;67(14):4916-23. doi: 10.1021/jo020230r.

Conjugate adducts obtained by base-induced 1,4-addition-elimination of various aryl/heteroaryl acetonitriles with 1-(2-arylcyclopropyl)-3,3-(bismethylthio)-2-propen-1-ones have been shown to undergo facile acid-induced domino carbocationic rearrangement yielding a variety of substituted tricyclic aromatic and heteroaromatic frameworks in high yields in a one-pot operation....

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Nandi S, Kumar UK, Ila H, et al. Domino carbocationic cyclization of functionalized cyclopropyl ketones: facile one-pot access to peri- and angularly fused polycyclic aromatic and heteroaromatic frameworks. J Org Chem. 2002;67(14):4916-23doi: 10.1021/jo020230r.
Nandi, S., Kumar, U. K., Ila, H., & Junjappa, H. (2002). Domino carbocationic cyclization of functionalized cyclopropyl ketones: facile one-pot access to peri- and angularly fused polycyclic aromatic and heteroaromatic frameworks. The Journal of organic chemistry, 67(14), 4916-23. https://doi.org/10.1021/jo020230r
Nandi, Sukumar, et al. "Domino carbocationic cyclization of functionalized cyclopropyl ketones: facile one-pot access to peri- and angularly fused polycyclic aromatic and heteroaromatic frameworks." The Journal of organic chemistry vol. 67,14 (2002): 4916-23. doi: https://doi.org/10.1021/jo020230r
Nandi S, Kumar UK, Ila H, Junjappa H. Domino carbocationic cyclization of functionalized cyclopropyl ketones: facile one-pot access to peri- and angularly fused polycyclic aromatic and heteroaromatic frameworks. J Org Chem. 2002 Jul 12;67(14):4916-23. doi: 10.1021/jo020230r. PMID: 12098306.
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Efficient synthesis of 4,4'-bi-1H-imidazol-2-ones from 5-amino-alpha-imino-1H-imidazole-4-acetonitriles and isocyanates.

The Journal of organic chemistry

Dias AM, Cabral I, Proença MF, Booth BL.
PMID: 12153252
J Org Chem. 2002 Aug 09;67(16):5546-52. doi: 10.1021/jo011192z.

Reactions of 5-amino-alpha-imino-1H-imidazole-4-acetonitriles 1 with alkyl and aryl isocyanates led to efficient syntheses of 5'-amino-5-imino-4,4'-bi-1H-imidazol-2-ones 3 formed by intramolecular cyclization of the corresponding 5-amino-alpha-(N-alkyl/arylcarbamoyl)imino-1H-imidazole-4-acetonitriles 2. The cyclization occurs only slowly in solution but is considerably accelerated by the addition...

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Dias AM, Cabral I, Proença MF, et al. Efficient synthesis of 4,4'-bi-1H-imidazol-2-ones from 5-amino-alpha-imino-1H-imidazole-4-acetonitriles and isocyanates. J Org Chem. 2002;67(16):5546-52doi: 10.1021/jo011192z.
Dias, A. M., Cabral, I., Proença, M. F., & Booth, B. L. (2002). Efficient synthesis of 4,4'-bi-1H-imidazol-2-ones from 5-amino-alpha-imino-1H-imidazole-4-acetonitriles and isocyanates. The Journal of organic chemistry, 67(16), 5546-52. https://doi.org/10.1021/jo011192z
Dias, Alice M, et al. "Efficient synthesis of 4,4'-bi-1H-imidazol-2-ones from 5-amino-alpha-imino-1H-imidazole-4-acetonitriles and isocyanates." The Journal of organic chemistry vol. 67,16 (2002): 5546-52. doi: https://doi.org/10.1021/jo011192z
Dias AM, Cabral I, Proença MF, Booth BL. Efficient synthesis of 4,4'-bi-1H-imidazol-2-ones from 5-amino-alpha-imino-1H-imidazole-4-acetonitriles and isocyanates. J Org Chem. 2002 Aug 09;67(16):5546-52. doi: 10.1021/jo011192z. PMID: 12153252.
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Low temperature properties of acetonitrile confined in MCM-41.

The journal of physical chemistry. B

Kittaka S, Iwashita T, Serizawa A, Kranishi M, Takahara S, Kuroda Y, Mori T, Yamaguchi T.
PMID: 16375278
J Phys Chem B. 2005 Dec 15;109(49):23162-9. doi: 10.1021/jp052476g.

The effect of confinement on the phase changes and dynamics of acetonitrile in mesoporous MCM-41 was studied by use of adsorption, FT-IR, DSC, and quasi-elastic neutron scattering (QENS) measurements. Acetonitrile molecules in a monolayer interact strongly with surface hydroxyls...

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Kittaka S, Iwashita T, Serizawa A, et al. Low temperature properties of acetonitrile confined in MCM-41. J Phys Chem B. 2005;109(49):23162-9doi: 10.1021/jp052476g.
Kittaka, S., Iwashita, T., Serizawa, A., Kranishi, M., Takahara, S., Kuroda, Y., Mori, T., & Yamaguchi, T. (2005). Low temperature properties of acetonitrile confined in MCM-41. The journal of physical chemistry. B, 109(49), 23162-9. https://doi.org/10.1021/jp052476g
Kittaka, Shigeharu, et al. "Low temperature properties of acetonitrile confined in MCM-41." The journal of physical chemistry. B vol. 109,49 (2005): 23162-9. doi: https://doi.org/10.1021/jp052476g
Kittaka S, Iwashita T, Serizawa A, Kranishi M, Takahara S, Kuroda Y, Mori T, Yamaguchi T. Low temperature properties of acetonitrile confined in MCM-41. J Phys Chem B. 2005 Dec 15;109(49):23162-9. doi: 10.1021/jp052476g. PMID: 16375278.
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Enantioselective Alkynylation of 2-Trifluoroacetyl Imidazoles Catalyzed by Bis-Cyclometalated Rhodium(III) Complexes Containing Pinene-Derived Ligands.

Chemistry (Weinheim an der Bergstrasse, Germany)

Zheng Y, Harms K, Zhang L, Meggers E.
PMID: 27312941
Chemistry. 2016 Aug 16;22(34):11977-81. doi: 10.1002/chem.201602372. Epub 2016 Jul 14.

Chiral rhodium(III) complexes containing two cyclometalating 2-phenyl-5,6-(S,S)-pinenopyridine ligands and two additional acetonitriles are introduced as excellent catalysts for the highly enantioselective alkynylation of 2-trifluoroacetyl imidazoles. Whereas the ligand-based chirality permits the straightforward synthesis of the complexes in a diastereomerically...

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Zheng Y, Harms K, Zhang L, et al. Enantioselective Alkynylation of 2-Trifluoroacetyl Imidazoles Catalyzed by Bis-Cyclometalated Rhodium(III) Complexes Containing Pinene-Derived Ligands. Chemistry. 2016;22(34):11977-81doi: 10.1002/chem.201602372.
Zheng, Y., Harms, K., Zhang, L., & Meggers, E. (2016). Enantioselective Alkynylation of 2-Trifluoroacetyl Imidazoles Catalyzed by Bis-Cyclometalated Rhodium(III) Complexes Containing Pinene-Derived Ligands. Chemistry (Weinheim an der Bergstrasse, Germany), 22(34), 11977-81. https://doi.org/10.1002/chem.201602372
Zheng, Yu, et al. "Enantioselective Alkynylation of 2-Trifluoroacetyl Imidazoles Catalyzed by Bis-Cyclometalated Rhodium(III) Complexes Containing Pinene-Derived Ligands." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,34 (2016): 11977-81. doi: https://doi.org/10.1002/chem.201602372
Zheng Y, Harms K, Zhang L, Meggers E. Enantioselective Alkynylation of 2-Trifluoroacetyl Imidazoles Catalyzed by Bis-Cyclometalated Rhodium(III) Complexes Containing Pinene-Derived Ligands. Chemistry. 2016 Aug 16;22(34):11977-81. doi: 10.1002/chem.201602372. Epub 2016 Jul 14. PMID: 27312941.
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A Catalytic Peterson-like Synthesis of Alkenyl Nitriles.

Organic letters

Lanari D, Alonzi M, Ferlin F, Santoro S, Vaccaro L.
PMID: 27187788
Org Lett. 2016 Jun 03;18(11):2680-3. doi: 10.1021/acs.orglett.6b01121. Epub 2016 May 17.

A heterogeneous fluoride catalyst was found to enable the straightforward formation of alkenyl nitriles from the reaction of aldehydes and simple or substituted acetonitriles, in the presence of commercially available silazanes and in solvent-free conditions. The protocol afforded the...

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Lanari D, Alonzi M, Ferlin F, et al. A Catalytic Peterson-like Synthesis of Alkenyl Nitriles. Org Lett. 2016;18(11):2680-3doi: 10.1021/acs.orglett.6b01121.
Lanari, D., Alonzi, M., Ferlin, F., Santoro, S., & Vaccaro, L. (2016). A Catalytic Peterson-like Synthesis of Alkenyl Nitriles. Organic letters, 18(11), 2680-3. https://doi.org/10.1021/acs.orglett.6b01121
Lanari, Daniela, et al. "A Catalytic Peterson-like Synthesis of Alkenyl Nitriles." Organic letters vol. 18,11 (2016): 2680-3. doi: https://doi.org/10.1021/acs.orglett.6b01121
Lanari D, Alonzi M, Ferlin F, Santoro S, Vaccaro L. A Catalytic Peterson-like Synthesis of Alkenyl Nitriles. Org Lett. 2016 Jun 03;18(11):2680-3. doi: 10.1021/acs.orglett.6b01121. Epub 2016 May 17. PMID: 27187788.
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Nucleofugal behavior of a β-shielded α-cyanovinyl carbanion.

Beilstein journal of organic chemistry

Knorr R, Schmidt B.
PMID: 30591825
Beilstein J Org Chem. 2018 Dec 11;14:3018-3024. doi: 10.3762/bjoc.14.281. eCollection 2018.

Sterically well-shielded against unsolicited Michael addition and polymerization reactions, α-metalated α-(1,1,3,3-tetramethylindan-2-ylidene)acetonitriles added reversibly to three small aldehydes and two bulky ketones at room temperature. Experimental conditions were determined for transfer of the nucleofugal title carbanion unit between different carbonyl...

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Knorr R, Schmidt B. Nucleofugal behavior of a β-shielded α-cyanovinyl carbanion. Beilstein J Org Chem. 2018;14:3018-3024doi: 10.3762/bjoc.14.281.
Knorr, R., & Schmidt, B. (2018). Nucleofugal behavior of a β-shielded α-cyanovinyl carbanion. Beilstein journal of organic chemistry, 143018-3024. https://doi.org/10.3762/bjoc.14.281
Knorr, Rudolf, and Schmidt, Barbara. "Nucleofugal behavior of a β-shielded α-cyanovinyl carbanion." Beilstein journal of organic chemistry vol. 14 (2018): 3018-3024. doi: https://doi.org/10.3762/bjoc.14.281
Knorr R, Schmidt B. Nucleofugal behavior of a β-shielded α-cyanovinyl carbanion. Beilstein J Org Chem. 2018 Dec 11;14:3018-3024. doi: 10.3762/bjoc.14.281. eCollection 2018. PMID: 30591825; PMCID: PMC6296431.
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Synthesis of Trifluoromethyl- and Ester Group-Substituted α-Carbolines via Iron-Catalyzed Tandem Cyclization Reaction.

The Journal of organic chemistry

Xu Y, Chen X, Gao Y, Yan Z, Wan C, Liu JB, Wang Z.
PMID: 32090568
J Org Chem. 2020 Mar 20;85(6):4354-4364. doi: 10.1021/acs.joc.0c00048. Epub 2020 Mar 05.

An efficient approach to prepare trifluoromethyl-α-carbolines and ester group-substituted α-carbolines via the tandem cyclization reaction of 2-(2-aminophenyl)acetonitriles and trifluoromethyl 1,3-diones or β,γ-unsaturated α-ketoesters was reported. The transformation proceeded smoothly in the presence of catalytic environmental-benign iron salts, which are...

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Xu Y, Chen X, Gao Y, et al. Synthesis of Trifluoromethyl- and Ester Group-Substituted α-Carbolines via Iron-Catalyzed Tandem Cyclization Reaction. J Org Chem. 2020;85(6):4354-4364doi: 10.1021/acs.joc.0c00048.
Xu, Y., Chen, X., Gao, Y., Yan, Z., Wan, C., Liu, J. B., & Wang, Z. (2020). Synthesis of Trifluoromethyl- and Ester Group-Substituted α-Carbolines via Iron-Catalyzed Tandem Cyclization Reaction. The Journal of organic chemistry, 85(6), 4354-4364. https://doi.org/10.1021/acs.joc.0c00048
Xu, Yumin, et al. "Synthesis of Trifluoromethyl- and Ester Group-Substituted α-Carbolines via Iron-Catalyzed Tandem Cyclization Reaction." The Journal of organic chemistry vol. 85,6 (2020): 4354-4364. doi: https://doi.org/10.1021/acs.joc.0c00048
Xu Y, Chen X, Gao Y, Yan Z, Wan C, Liu JB, Wang Z. Synthesis of Trifluoromethyl- and Ester Group-Substituted α-Carbolines via Iron-Catalyzed Tandem Cyclization Reaction. J Org Chem. 2020 Mar 20;85(6):4354-4364. doi: 10.1021/acs.joc.0c00048. Epub 2020 Mar 05. PMID: 32090568.
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Computational studies of inclusion phenomena and synthesis of a novel and selective molecular receptor for 1,4-disubstituted benzenes and 4,4'-disubstituted biphenyls.

The Journal of organic chemistry

Macias AT, Kumar KA, Marchand AP, Evanseck JD.
PMID: 10774029
J Org Chem. 2000 Apr 07;65(7):2083-9. doi: 10.1021/jo991669v.

A new tetracationic molecular receptor has been synthesized and studied by semiempirical molecular orbital theory. This novel macrocycle, 1(4+), derived from pentacyclo[5.0.0.0.(2,6)0.(3,10)0(5,9)]undecane-8,11-dione (PCU-8,11-dione), structurally resembles cyclobis(paraquat-p-phenylene), 2(4+), in which a xylyl group has been replaced by a PCU unit....

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Macias AT, Kumar KA, Marchand AP, et al. Computational studies of inclusion phenomena and synthesis of a novel and selective molecular receptor for 1,4-disubstituted benzenes and 4,4'-disubstituted biphenyls. J Org Chem. 2000;65(7):2083-9doi: 10.1021/jo991669v.
Macias, A. T., Kumar, K. A., Marchand, A. P., & Evanseck, J. D. (2000). Computational studies of inclusion phenomena and synthesis of a novel and selective molecular receptor for 1,4-disubstituted benzenes and 4,4'-disubstituted biphenyls. The Journal of organic chemistry, 65(7), 2083-9. https://doi.org/10.1021/jo991669v
Macias, et al. "Computational studies of inclusion phenomena and synthesis of a novel and selective molecular receptor for 1,4-disubstituted benzenes and 4,4'-disubstituted biphenyls." The Journal of organic chemistry vol. 65,7 (2000): 2083-9. doi: https://doi.org/10.1021/jo991669v
Macias AT, Kumar KA, Marchand AP, Evanseck JD. Computational studies of inclusion phenomena and synthesis of a novel and selective molecular receptor for 1,4-disubstituted benzenes and 4,4'-disubstituted biphenyls. J Org Chem. 2000 Apr 07;65(7):2083-9. doi: 10.1021/jo991669v. PMID: 10774029.
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Showing 13 to 24 of 45 entries