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The Synthesis and Characterization of Highly Fluorescent Polycyclic Azaborine Chromophores.

The Journal of organic chemistry

Saint-Louis CJ, Magill LL, Wilson JA, Schroeder AR, Harrell SE, Jackson NS, Trindell JA, Kim S, Fisch AR, Munro L, Catalano VJ, Webster CE, Vaughan PP, Molek KS, Schrock AK, Huggins MT.
PMID: 27704820
J Org Chem. 2016 Nov 18;81(22):10955-10963. doi: 10.1021/acs.joc.6b01998. Epub 2016 Oct 25.

Six new heteroaromatic polycyclic azaborine chromophores were designed, synthesized, and investigated as easily tunable high-luminescent organic materials. The impact of the nitrogen-boron-hydroxy (N-BOH) unit in the azaborines was investigated by comparison with their N-carbonyl analogs. Insertion of the N-B(OH)-C...

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Saint-Louis CJ, Magill LL, Wilson JA, et al. The Synthesis and Characterization of Highly Fluorescent Polycyclic Azaborine Chromophores. J Org Chem. 2016;81(22):10955-10963doi: 10.1021/acs.joc.6b01998.
Saint-Louis, C. J., Magill, L. L., Wilson, J. A., Schroeder, A. R., Harrell, S. E., Jackson, N. S., Trindell, J. A., Kim, S., Fisch, A. R., Munro, L., Catalano, V. J., Webster, C. E., Vaughan, P. P., Molek, K. S., Schrock, A. K., & Huggins, M. T. (2016). The Synthesis and Characterization of Highly Fluorescent Polycyclic Azaborine Chromophores. The Journal of organic chemistry, 81(22), 10955-10963. https://doi.org/10.1021/acs.joc.6b01998
Saint-Louis, Carl Jacky, et al. "The Synthesis and Characterization of Highly Fluorescent Polycyclic Azaborine Chromophores." The Journal of organic chemistry vol. 81,22 (2016): 10955-10963. doi: https://doi.org/10.1021/acs.joc.6b01998
Saint-Louis CJ, Magill LL, Wilson JA, Schroeder AR, Harrell SE, Jackson NS, Trindell JA, Kim S, Fisch AR, Munro L, Catalano VJ, Webster CE, Vaughan PP, Molek KS, Schrock AK, Huggins MT. The Synthesis and Characterization of Highly Fluorescent Polycyclic Azaborine Chromophores. J Org Chem. 2016 Nov 18;81(22):10955-10963. doi: 10.1021/acs.joc.6b01998. Epub 2016 Oct 25. PMID: 27704820.
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The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Scharnagel D, Müller A, Prause F, Eck M, Goller J, Milius W, Breuning M.
PMID: 26230668
Chemistry. 2015 Aug 24;21(35):12488-500. doi: 10.1002/chem.201502090. Epub 2015 Jul 31.

The first modular and flexible synthesis of core-chiral bispidines was achieved by using an "inside-out" strategy. The key intermediate, a NBoc-activated bispidine lactam, was constructed in enantiomerically pure form from a chirally modified β-amino acid and 2-(acetoxymethyl)acrylonitrile in just...

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Scharnagel D, Müller A, Prause F, et al. The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions. Chemistry. 2015;21(35):12488-500doi: 10.1002/chem.201502090.
Scharnagel, D., Müller, A., Prause, F., Eck, M., Goller, J., Milius, W., & Breuning, M. (2015). The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions. Chemistry (Weinheim an der Bergstrasse, Germany), 21(35), 12488-500. https://doi.org/10.1002/chem.201502090
Scharnagel, Dagmar, et al. "The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,35 (2015): 12488-500. doi: https://doi.org/10.1002/chem.201502090
Scharnagel D, Müller A, Prause F, Eck M, Goller J, Milius W, Breuning M. The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions. Chemistry. 2015 Aug 24;21(35):12488-500. doi: 10.1002/chem.201502090. Epub 2015 Jul 31. PMID: 26230668.
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Achieving Molecular Complexity via Stereoselective Multiple Domino Reactions Promoted by a Secondary Amine Organocatalyst.

Accounts of chemical research

Chauhan P, Mahajan S, Enders D.
PMID: 29125741
Acc Chem Res. 2017 Nov 21;50(11):2809-2821. doi: 10.1021/acs.accounts.7b00406. Epub 2017 Nov 10.

In the last two decades, organocatalysis has emerged as an intensively investigated and rapidly growing area of research facilitating many known and many new transformations to provide efficient novel entries to complex molecules of high stereochemical purity. The organocatalysts...

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Chauhan P, Mahajan S, Enders D. Achieving Molecular Complexity via Stereoselective Multiple Domino Reactions Promoted by a Secondary Amine Organocatalyst. Acc Chem Res. 2017;50(11):2809-2821doi: 10.1021/acs.accounts.7b00406.
Chauhan, P., Mahajan, S., & Enders, D. (2017). Achieving Molecular Complexity via Stereoselective Multiple Domino Reactions Promoted by a Secondary Amine Organocatalyst. Accounts of chemical research, 50(11), 2809-2821. https://doi.org/10.1021/acs.accounts.7b00406
Chauhan, Pankaj, et al. "Achieving Molecular Complexity via Stereoselective Multiple Domino Reactions Promoted by a Secondary Amine Organocatalyst." Accounts of chemical research vol. 50,11 (2017): 2809-2821. doi: https://doi.org/10.1021/acs.accounts.7b00406
Chauhan P, Mahajan S, Enders D. Achieving Molecular Complexity via Stereoselective Multiple Domino Reactions Promoted by a Secondary Amine Organocatalyst. Acc Chem Res. 2017 Nov 21;50(11):2809-2821. doi: 10.1021/acs.accounts.7b00406. Epub 2017 Nov 10. PMID: 29125741.
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Rh(III)-Catalyzed Carbocyclization of 3-(Indolin-1-yl)-3-oxopropanenitriles with Alkynes and Alkenes through C-H Activation.

Organic letters

Zhou T, Wang Y, Li B, Wang B.
PMID: 27648487
Org Lett. 2016 Oct 07;18(19):5066-5069. doi: 10.1021/acs.orglett.6b02521. Epub 2016 Sep 20.

Rh(III)-catalyzed carbocyclization reactions of 3-(indolin-1-yl)-3-oxopropanenitriles with alkynes and alkenes have been developed to form 1,7-fused indolines through C-H activation. These reactions have a broad range of substrates and high yields. Unsymmetrical aryl-alkyl substituted alkynes proceeded smoothly with high regioselectivity....

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Zhou T, Wang Y, Li B, et al. Rh(III)-Catalyzed Carbocyclization of 3-(Indolin-1-yl)-3-oxopropanenitriles with Alkynes and Alkenes through C-H Activation. Org Lett. 2016;18(19):5066-5069doi: 10.1021/acs.orglett.6b02521.
Zhou, T., Wang, Y., Li, B., & Wang, B. (2016). Rh(III)-Catalyzed Carbocyclization of 3-(Indolin-1-yl)-3-oxopropanenitriles with Alkynes and Alkenes through C-H Activation. Organic letters, 18(19), 5066-5069. https://doi.org/10.1021/acs.orglett.6b02521
Zhou, Tao, et al. "Rh(III)-Catalyzed Carbocyclization of 3-(Indolin-1-yl)-3-oxopropanenitriles with Alkynes and Alkenes through C-H Activation." Organic letters vol. 18,19 (2016): 5066-5069. doi: https://doi.org/10.1021/acs.orglett.6b02521
Zhou T, Wang Y, Li B, Wang B. Rh(III)-Catalyzed Carbocyclization of 3-(Indolin-1-yl)-3-oxopropanenitriles with Alkynes and Alkenes through C-H Activation. Org Lett. 2016 Oct 07;18(19):5066-5069. doi: 10.1021/acs.orglett.6b02521. Epub 2016 Sep 20. PMID: 27648487.
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Gold(I)-catalyzed cycloisomerizations and alkoxycyclizations of ortho-(alkynyl)styrenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Sanjuán AM, Rashid MA, García-García P, Martínez-Cuezva A, Fernández-Rodríguez MA, Rodríguez F, Sanz R.
PMID: 25557166
Chemistry. 2015 Feb 09;21(7):3042-52. doi: 10.1002/chem.201405789. Epub 2014 Dec 29.

Indenes and related polycyclic structures have been efficiently synthesized by gold(I)-catalyzed cycloisomerizations of appropriate ortho-(alkynyl)styrenes. Disubstitution at the terminal position of the olefin was demonstrated to be essential to obtain products originating from a formal 5-endo-dig cyclization. Interestingly, a...

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Sanjuán AM, Rashid MA, García-García P, et al. Gold(I)-catalyzed cycloisomerizations and alkoxycyclizations of ortho-(alkynyl)styrenes. Chemistry. 2014;21(7):3042-52doi: 10.1002/chem.201405789.
Sanjuán, A. M., Rashid, M. A., García-García, P., Martínez-Cuezva, A., Fernández-Rodríguez, M. A., Rodríguez, F., & Sanz, R. (2015). Gold(I)-catalyzed cycloisomerizations and alkoxycyclizations of ortho-(alkynyl)styrenes. Chemistry (Weinheim an der Bergstrasse, Germany), 21(7), 3042-52. https://doi.org/10.1002/chem.201405789
Sanjuán, Ana M, et al. "Gold(I)-catalyzed cycloisomerizations and alkoxycyclizations of ortho-(alkynyl)styrenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,7 (2015): 3042-52. doi: https://doi.org/10.1002/chem.201405789
Sanjuán AM, Rashid MA, García-García P, Martínez-Cuezva A, Fernández-Rodríguez MA, Rodríguez F, Sanz R. Gold(I)-catalyzed cycloisomerizations and alkoxycyclizations of ortho-(alkynyl)styrenes. Chemistry. 2015 Feb 09;21(7):3042-52. doi: 10.1002/chem.201405789. Epub 2014 Dec 29. PMID: 25557166.
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Synthesis of aza polycyclic compounds derived from pyrrolidine, indolizidine, and indole via intramolecular Diels-Alder cycloadditions of neutral 2-azadienes.

The Journal of organic chemistry

Palacios F, Alonso C, Amezua P, Rubiales G.
PMID: 11895415
J Org Chem. 2002 Mar 22;67(6):1941-6. doi: 10.1021/jo016325v.

A method for the preparation of novel oxaza and diaza polycyclic 9-oxa-4-azaphenanthrene, 5H-pyrido[2,3-a]pyrrolizine, 5H,6H-pyrido[3,2-g]indolizine, and 5H,6H-indeno[2,1-a]indole is described, based on tandem reactions: aza-Wittig reaction of N-vinylic phosphazenes with functionalized aldehydes and an intramolecular aza-Diels-Alder reaction.

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Palacios F, Alonso C, Amezua P, et al. Synthesis of aza polycyclic compounds derived from pyrrolidine, indolizidine, and indole via intramolecular Diels-Alder cycloadditions of neutral 2-azadienes. J Org Chem. 2002;67(6):1941-6doi: 10.1021/jo016325v.
Palacios, F., Alonso, C., Amezua, P., & Rubiales, G. (2002). Synthesis of aza polycyclic compounds derived from pyrrolidine, indolizidine, and indole via intramolecular Diels-Alder cycloadditions of neutral 2-azadienes. The Journal of organic chemistry, 67(6), 1941-6. https://doi.org/10.1021/jo016325v
Palacios, Francisco, et al. "Synthesis of aza polycyclic compounds derived from pyrrolidine, indolizidine, and indole via intramolecular Diels-Alder cycloadditions of neutral 2-azadienes." The Journal of organic chemistry vol. 67,6 (2002): 1941-6. doi: https://doi.org/10.1021/jo016325v
Palacios F, Alonso C, Amezua P, Rubiales G. Synthesis of aza polycyclic compounds derived from pyrrolidine, indolizidine, and indole via intramolecular Diels-Alder cycloadditions of neutral 2-azadienes. J Org Chem. 2002 Mar 22;67(6):1941-6. doi: 10.1021/jo016325v. PMID: 11895415.
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Cascade cyclization: an easy access to highly unsaturated polycyclic ring systems through a tandem stille/[4 + 2] reaction under mild conditions.

Organic letters

Brückner S, Abraham E, Klotz P, Suffert J.
PMID: 12323026
Org Lett. 2002 Oct 03;4(20):3391-3. doi: 10.1021/ol0264253.

The synthesis of several polycyclic compounds 1a-c, 2, and 3 has been performed through a tandem Stille/[4 + 2] cascade reaction from cyclic bis(enoltrifluomethanesulfonate) 4a-c, 5, and 6, respectively. The reaction proceeds very efficiently in a one-pot operation at...

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Brückner S, Abraham E, Klotz P, et al. Cascade cyclization: an easy access to highly unsaturated polycyclic ring systems through a tandem stille/[4 + 2] reaction under mild conditions. Org Lett. 2002;4(20):3391-3doi: 10.1021/ol0264253.
Brückner, S., Abraham, E., Klotz, P., & Suffert, J. (2002). Cascade cyclization: an easy access to highly unsaturated polycyclic ring systems through a tandem stille/[4 + 2] reaction under mild conditions. Organic letters, 4(20), 3391-3. https://doi.org/10.1021/ol0264253
Brückner, Sébastien, et al. "Cascade cyclization: an easy access to highly unsaturated polycyclic ring systems through a tandem stille/[4 + 2] reaction under mild conditions." Organic letters vol. 4,20 (2002): 3391-3. doi: https://doi.org/10.1021/ol0264253
Brückner S, Abraham E, Klotz P, Suffert J. Cascade cyclization: an easy access to highly unsaturated polycyclic ring systems through a tandem stille/[4 + 2] reaction under mild conditions. Org Lett. 2002 Oct 03;4(20):3391-3. doi: 10.1021/ol0264253. PMID: 12323026.
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Doyle-Kirmse reaction of allylic sulfides with diazoalkane-free (2-furyl)carbenoid transfer.

Organic letters

Kato Y, Miki K, Nishino F, Ohe K, Uemura S.
PMID: 12868873
Org Lett. 2003 Jul 24;5(15):2619-21. doi: 10.1021/ol034731q.

[reaction: see text] In the presence of rhodium catalyst, (2-furyl)carbenoids generated from conjugated ene-yne-carbonyl compounds 1 efficiently undergo carbene transfer reactions with allylic sulfides followed by [2,3]sigmatropic rearrangement of sulfur ylides to give furan-containing sulfides in good yields. When...

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Kato Y, Miki K, Nishino F, et al. Doyle-Kirmse reaction of allylic sulfides with diazoalkane-free (2-furyl)carbenoid transfer. Org Lett. 2003;5(15):2619-21doi: 10.1021/ol034731q.
Kato, Y., Miki, K., Nishino, F., Ohe, K., & Uemura, S. (2003). Doyle-Kirmse reaction of allylic sulfides with diazoalkane-free (2-furyl)carbenoid transfer. Organic letters, 5(15), 2619-21. https://doi.org/10.1021/ol034731q
Kato, Yumiko, et al. "Doyle-Kirmse reaction of allylic sulfides with diazoalkane-free (2-furyl)carbenoid transfer." Organic letters vol. 5,15 (2003): 2619-21. doi: https://doi.org/10.1021/ol034731q
Kato Y, Miki K, Nishino F, Ohe K, Uemura S. Doyle-Kirmse reaction of allylic sulfides with diazoalkane-free (2-furyl)carbenoid transfer. Org Lett. 2003 Jul 24;5(15):2619-21. doi: 10.1021/ol034731q. PMID: 12868873.
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Photochemistry of o-pyrrolylstilbenes and formation of spiro-2H-pyrroles and their rearrangement to dihydroindoles.

The Journal of organic chemistry

Basarić N, Marinić E, Sindler-Kulyk M.
PMID: 17137365
J Org Chem. 2006 Dec 08;71(25):9382-92. doi: 10.1021/jo061435t.

Excited states of stilbenylpyrroles 1a-1c deactivate by two photochemical processes: cis-trans-isomerization and hydrogen transfer of NH to the stilbene double bond. NH-transfer results in the formation of two quinone dimethane intermediates, 10 and 11, and biradicals 12. Intramolecular cyclization...

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Basarić N, Marinić E, Sindler-Kulyk M. Photochemistry of o-pyrrolylstilbenes and formation of spiro-2H-pyrroles and their rearrangement to dihydroindoles. J Org Chem. 2006;71(25):9382-92doi: 10.1021/jo061435t.
Basarić, N., Marinić, E., & Sindler-Kulyk, M. (2006). Photochemistry of o-pyrrolylstilbenes and formation of spiro-2H-pyrroles and their rearrangement to dihydroindoles. The Journal of organic chemistry, 71(25), 9382-92. https://doi.org/10.1021/jo061435t
Basarić, Nikola, et al. "Photochemistry of o-pyrrolylstilbenes and formation of spiro-2H-pyrroles and their rearrangement to dihydroindoles." The Journal of organic chemistry vol. 71,25 (2006): 9382-92. doi: https://doi.org/10.1021/jo061435t
Basarić N, Marinić E, Sindler-Kulyk M. Photochemistry of o-pyrrolylstilbenes and formation of spiro-2H-pyrroles and their rearrangement to dihydroindoles. J Org Chem. 2006 Dec 08;71(25):9382-92. doi: 10.1021/jo061435t. PMID: 17137365.
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Polycyclic compounds from aminopolyols and alpha-dicarbonyls: structure and application in the synthesis of exoditopic ligands.

Organic & biomolecular chemistry

Giovenzana GB, Palmisano G, Del Grosso E, Giovannelli L, Penoni A, Pilati T.
PMID: 15827646
Org Biomol Chem. 2005 Apr 21;3(8):1489-94. doi: 10.1039/b500580a. Epub 2005 Mar 15.

The structure and stereochemistry of the crystalline 2 : 2 condensation product ("glytham") of glyoxal and tris(hydroxymethyl)aminomethane was conclusively determined by X-ray diffractometric analysis. The singular disposition of the heteroatoms suggests the employment of glytham as starting material for...

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Giovenzana GB, Palmisano G, Del Grosso E, et al. Polycyclic compounds from aminopolyols and alpha-dicarbonyls: structure and application in the synthesis of exoditopic ligands. Org Biomol Chem. 2005;3(8):1489-94doi: 10.1039/b500580a.
Giovenzana, G. B., Palmisano, G., Del Grosso, E., Giovannelli, L., Penoni, A., & Pilati, T. (2005). Polycyclic compounds from aminopolyols and alpha-dicarbonyls: structure and application in the synthesis of exoditopic ligands. Organic & biomolecular chemistry, 3(8), 1489-94. https://doi.org/10.1039/b500580a
Giovenzana, Giovanni B, et al. "Polycyclic compounds from aminopolyols and alpha-dicarbonyls: structure and application in the synthesis of exoditopic ligands." Organic & biomolecular chemistry vol. 3,8 (2005): 1489-94. doi: https://doi.org/10.1039/b500580a
Giovenzana GB, Palmisano G, Del Grosso E, Giovannelli L, Penoni A, Pilati T. Polycyclic compounds from aminopolyols and alpha-dicarbonyls: structure and application in the synthesis of exoditopic ligands. Org Biomol Chem. 2005 Apr 21;3(8):1489-94. doi: 10.1039/b500580a. Epub 2005 Mar 15. PMID: 15827646.
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QTAIM N-center delocalization indices as descriptors of aromaticity in mono and poly heterocycles.

Journal of computational chemistry

Mandado M, González-Moa MJ, Mosquera RA.
PMID: 17063477
J Comput Chem. 2007 Jan 15;28(1):127-36. doi: 10.1002/jcc.20468.

The implementation of the n-center electron delocalization indices, n-DIs, and n-order electron localization indices, n-LIs, within the framework of the quantum theory of atoms in molecules, QTAIM, is performed. n-DIs are shown to be very useful to study the...

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Mandado M, González-Moa MJ, Mosquera RA. QTAIM N-center delocalization indices as descriptors of aromaticity in mono and poly heterocycles. J Comput Chem. 2007;28(1):127-36doi: 10.1002/jcc.20468.
Mandado, M., González-Moa, M. J., & Mosquera, R. A. (2007). QTAIM N-center delocalization indices as descriptors of aromaticity in mono and poly heterocycles. Journal of computational chemistry, 28(1), 127-36. https://doi.org/10.1002/jcc.20468
Mandado, Marcos, et al. "QTAIM N-center delocalization indices as descriptors of aromaticity in mono and poly heterocycles." Journal of computational chemistry vol. 28,1 (2007): 127-36. doi: https://doi.org/10.1002/jcc.20468
Mandado M, González-Moa MJ, Mosquera RA. QTAIM N-center delocalization indices as descriptors of aromaticity in mono and poly heterocycles. J Comput Chem. 2007 Jan 15;28(1):127-36. doi: 10.1002/jcc.20468. PMID: 17063477.
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Cyclopropenes in the 1,3-dipolar cycloaddition with carbonyl ylides: experimental and theoretical evidence for the enhancement of sigma-withdrawal in 3-substituted-cyclopropenes.

The Journal of organic chemistry

Diev VV, Kostikov RR, Gleiter R, Molchanov AP.
PMID: 16709045
J Org Chem. 2006 May 26;71(11):4066-77. doi: 10.1021/jo0600656.

The carbonyl ylide dipoles generated by the dirhodium tetra-acetate-catalyzed decomposition of diazocarbonyl precursors 1, 5, and 8 cycloadd to 3-substituted 1,2-diphenylcyclopropenes 3a-e and 3,3-disubstituted cyclopropenes 13, 14, 19, and 20 to give polycyclic compounds with 8-oxatricyclo[3.2.1.0(2,4)]octane and 9-oxatricyclo[3.3.1.0(2,4)]nonane frameworks....

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Diev VV, Kostikov RR, Gleiter R, et al. Cyclopropenes in the 1,3-dipolar cycloaddition with carbonyl ylides: experimental and theoretical evidence for the enhancement of sigma-withdrawal in 3-substituted-cyclopropenes. J Org Chem. 2006;71(11):4066-77doi: 10.1021/jo0600656.
Diev, V. V., Kostikov, R. R., Gleiter, R., & Molchanov, A. P. (2006). Cyclopropenes in the 1,3-dipolar cycloaddition with carbonyl ylides: experimental and theoretical evidence for the enhancement of sigma-withdrawal in 3-substituted-cyclopropenes. The Journal of organic chemistry, 71(11), 4066-77. https://doi.org/10.1021/jo0600656
Diev, Vyacheslav V, et al. "Cyclopropenes in the 1,3-dipolar cycloaddition with carbonyl ylides: experimental and theoretical evidence for the enhancement of sigma-withdrawal in 3-substituted-cyclopropenes." The Journal of organic chemistry vol. 71,11 (2006): 4066-77. doi: https://doi.org/10.1021/jo0600656
Diev VV, Kostikov RR, Gleiter R, Molchanov AP. Cyclopropenes in the 1,3-dipolar cycloaddition with carbonyl ylides: experimental and theoretical evidence for the enhancement of sigma-withdrawal in 3-substituted-cyclopropenes. J Org Chem. 2006 May 26;71(11):4066-77. doi: 10.1021/jo0600656. PMID: 16709045.
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