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Multifaceted α-Enaminone: Adaptable Building Block for Synthesis of Heterocyclic Scaffolds Through Conceptually Distinct 1,2-, 1,3-, 1,4-, and C-O Bond Forming Annulations.

The Journal of organic chemistry

Lankri D, Albarghouti G, Mahameed M, Tsvelikhovsky D.
PMID: 28627896
J Org Chem. 2017 Jul 21;82(14):7101-7113. doi: 10.1021/acs.joc.7b00516. Epub 2017 Jun 30.

The new reactivity of α,β-unsaturated enaminones driven by their "dual electronic attitude" is reported. We introduce unexplored, α-enaminone synthones and reveal the unusual functionalities of these building blocks. The feasibility of this new concept is demonstrated in the direct...

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Lankri D, Albarghouti G, Mahameed M, et al. Multifaceted α-Enaminone: Adaptable Building Block for Synthesis of Heterocyclic Scaffolds Through Conceptually Distinct 1,2-, 1,3-, 1,4-, and C-O Bond Forming Annulations. J Org Chem. 2017;82(14):7101-7113doi: 10.1021/acs.joc.7b00516.
Lankri, D., Albarghouti, G., Mahameed, M., & Tsvelikhovsky, D. (2017). Multifaceted α-Enaminone: Adaptable Building Block for Synthesis of Heterocyclic Scaffolds Through Conceptually Distinct 1,2-, 1,3-, 1,4-, and C-O Bond Forming Annulations. The Journal of organic chemistry, 82(14), 7101-7113. https://doi.org/10.1021/acs.joc.7b00516
Lankri, David, et al. "Multifaceted α-Enaminone: Adaptable Building Block for Synthesis of Heterocyclic Scaffolds Through Conceptually Distinct 1,2-, 1,3-, 1,4-, and C-O Bond Forming Annulations." The Journal of organic chemistry vol. 82,14 (2017): 7101-7113. doi: https://doi.org/10.1021/acs.joc.7b00516
Lankri D, Albarghouti G, Mahameed M, Tsvelikhovsky D. Multifaceted α-Enaminone: Adaptable Building Block for Synthesis of Heterocyclic Scaffolds Through Conceptually Distinct 1,2-, 1,3-, 1,4-, and C-O Bond Forming Annulations. J Org Chem. 2017 Jul 21;82(14):7101-7113. doi: 10.1021/acs.joc.7b00516. Epub 2017 Jun 30. PMID: 28627896.
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Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction.

The Journal of organic chemistry

Wan JP, Lin Y, Huang Q, Liu Y.
PMID: 25003698
J Org Chem. 2014 Aug 01;79(15):7232-8. doi: 10.1021/jo501292q. Epub 2014 Jul 15.

The three-component reactions of enals, electron-deficient alkynes, and hydroxyl-functionalized primary amines for the highly diastereoselective construction of dihydro-3H-benzo[4,5]oxazolo[3,2-a]pyridines, hexahydropyrido[2,1-b][1,3]oxazines, and tetrahydro-2H-oxazolo[3,2-a]pyridines have been achieved. Domino formation of one C-C, two C-N, and one C-O bonds are furnished in these...

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Wan JP, Lin Y, Huang Q, et al. Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction. J Org Chem. 2014;79(15):7232-8doi: 10.1021/jo501292q.
Wan, J. P., Lin, Y., Huang, Q., & Liu, Y. (2014). Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction. The Journal of organic chemistry, 79(15), 7232-8. https://doi.org/10.1021/jo501292q
Wan, Jie-Ping, et al. "Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction." The Journal of organic chemistry vol. 79,15 (2014): 7232-8. doi: https://doi.org/10.1021/jo501292q
Wan JP, Lin Y, Huang Q, Liu Y. Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction. J Org Chem. 2014 Aug 01;79(15):7232-8. doi: 10.1021/jo501292q. Epub 2014 Jul 15. PMID: 25003698.
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Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group.

Chemistry (Weinheim an der Bergstrasse, Germany)

Yuan YC, Yang HB, Tang XY, Wei Y, Shi M.
PMID: 26868457
Chemistry. 2016 Apr 04;22(15):5146-50. doi: 10.1002/chem.201505224. Epub 2016 Feb 26.

A novel intramolecular oxycyanation of methylenecyclopropanes is reported that proceeds through oxidative cleavage of the N-CN bond and subsequent palladium transfer from N to O of the amide group. A range of substituted benzo[d][1,3]oxazines with a cyano group are...

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Yuan YC, Yang HB, Tang XY, et al. Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group. Chemistry. 2016;22(15):5146-50doi: 10.1002/chem.201505224.
Yuan, Y. C., Yang, H. B., Tang, X. Y., Wei, Y., & Shi, M. (2016). Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group. Chemistry (Weinheim an der Bergstrasse, Germany), 22(15), 5146-50. https://doi.org/10.1002/chem.201505224
Yuan, Yu-Chao, et al. "Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,15 (2016): 5146-50. doi: https://doi.org/10.1002/chem.201505224
Yuan YC, Yang HB, Tang XY, Wei Y, Shi M. Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group. Chemistry. 2016 Apr 04;22(15):5146-50. doi: 10.1002/chem.201505224. Epub 2016 Feb 26. PMID: 26868457.
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Substituent influences on the stability of the ring and chain tautomers in 1,3-O,N-heterocyclic systems: characterization by 13C NMR chemical shifts, PM3 charge densities, and isodesmic reactions.

The Journal of organic chemistry

Neuvonen K, Fülöp F, Neuvonen H, Koch A, Kleinpeter E, Pihlaja K.
PMID: 11397144
J Org Chem. 2001 Jun 15;66(12):4132-40. doi: 10.1021/jo001114w.

Substituent effects on the stabilities of the ring and chain forms in a tautomeric equilibrium of five series of 2-phenyloxazolidines or -perhydro-1,3-oxazines possessing nine different substitutions at the phenyl moiety have been studied with the aid of 13C NMR...

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Neuvonen K, Fülöp F, Neuvonen H, et al. Substituent influences on the stability of the ring and chain tautomers in 1,3-O,N-heterocyclic systems: characterization by 13C NMR chemical shifts, PM3 charge densities, and isodesmic reactions. J Org Chem. 2001;66(12):4132-40doi: 10.1021/jo001114w.
Neuvonen, K., Fülöp, F., Neuvonen, H., Koch, A., Kleinpeter, E., & Pihlaja, K. (2001). Substituent influences on the stability of the ring and chain tautomers in 1,3-O,N-heterocyclic systems: characterization by 13C NMR chemical shifts, PM3 charge densities, and isodesmic reactions. The Journal of organic chemistry, 66(12), 4132-40. https://doi.org/10.1021/jo001114w
Neuvonen, K, et al. "Substituent influences on the stability of the ring and chain tautomers in 1,3-O,N-heterocyclic systems: characterization by 13C NMR chemical shifts, PM3 charge densities, and isodesmic reactions." The Journal of organic chemistry vol. 66,12 (2001): 4132-40. doi: https://doi.org/10.1021/jo001114w
Neuvonen K, Fülöp F, Neuvonen H, Koch A, Kleinpeter E, Pihlaja K. Substituent influences on the stability of the ring and chain tautomers in 1,3-O,N-heterocyclic systems: characterization by 13C NMR chemical shifts, PM3 charge densities, and isodesmic reactions. J Org Chem. 2001 Jun 15;66(12):4132-40. doi: 10.1021/jo001114w. PMID: 11397144.
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Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles.

The Journal of organic chemistry

Pinho e Melo TM, Lopes CS, Gonsalves AM, Beja AM, Paixão JA, Silva MR, da Veiga LA.
PMID: 11777440
J Org Chem. 2002 Jan 11;67(1):66-71. doi: 10.1021/jo010504v.

Nucleophilic substitution reactions of 2-halo-2H-azirines 1a, 1b, 1d, and 1e with potassium phthalimide and aniline allowed the preparation of new substituted 2H-azirines 2-5. The reactions of 2-bromo-2H-azirine 1a with methylamine led to the synthesis of alpha-diimines 7 and 8....

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Pinho e Melo TM, Lopes CS, Gonsalves AM, et al. Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles. J Org Chem. 2002;67(1):66-71doi: 10.1021/jo010504v.
Pinho e Melo, T. M., Lopes, C. S., Gonsalves, A. M., Beja, A. M., Paixão, J. A., Silva, M. R., & da Veiga, L. A. (2002). Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles. The Journal of organic chemistry, 67(1), 66-71. https://doi.org/10.1021/jo010504v
Pinho e Melo, Teresa M V D, et al. "Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles." The Journal of organic chemistry vol. 67,1 (2002): 66-71. doi: https://doi.org/10.1021/jo010504v
Pinho e Melo TM, Lopes CS, Gonsalves AM, Beja AM, Paixão JA, Silva MR, da Veiga LA. Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles. J Org Chem. 2002 Jan 11;67(1):66-71. doi: 10.1021/jo010504v. PMID: 11777440.
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Modeling NMR parameters by DFT methods as an aid to the conformational analysis of cis-fused 7a(8a)-methyl octa(hexa)hydrocyclopenta[d][1,3]oxazines and [3,1]benzoxazines.

Journal of the American Chemical Society

Tähtinen P, Bagno A, Klika KD, Pihlaja K.
PMID: 12683833
J Am Chem Soc. 2003 Apr 16;125(15):4609-18. doi: 10.1021/ja021237t.

The energies of the preferred conformations of four 7a-methyl octa(or hexa)hydrocyclopenta[d][1,3]oxazines, five 8a-methyl octa(or hexa)hydro[3,1]benzoxazines, and 8a-methyl hexahydro[1,3]benzoxazinone, all cis-fused, were investigated by DFT methods. Following geometry optimization at the B3LYP/6-31G(d,p) level, both the proton chemical shifts and the...

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Tähtinen P, Bagno A, Klika KD, et al. Modeling NMR parameters by DFT methods as an aid to the conformational analysis of cis-fused 7a(8a)-methyl octa(hexa)hydrocyclopenta[d][1,3]oxazines and [3,1]benzoxazines. J Am Chem Soc. 2003;125(15):4609-18doi: 10.1021/ja021237t.
Tähtinen, P., Bagno, A., Klika, K. D., & Pihlaja, K. (2003). Modeling NMR parameters by DFT methods as an aid to the conformational analysis of cis-fused 7a(8a)-methyl octa(hexa)hydrocyclopenta[d][1,3]oxazines and [3,1]benzoxazines. Journal of the American Chemical Society, 125(15), 4609-18. https://doi.org/10.1021/ja021237t
Tähtinen, Petri, et al. "Modeling NMR parameters by DFT methods as an aid to the conformational analysis of cis-fused 7a(8a)-methyl octa(hexa)hydrocyclopenta[d][1,3]oxazines and [3,1]benzoxazines." Journal of the American Chemical Society vol. 125,15 (2003): 4609-18. doi: https://doi.org/10.1021/ja021237t
Tähtinen P, Bagno A, Klika KD, Pihlaja K. Modeling NMR parameters by DFT methods as an aid to the conformational analysis of cis-fused 7a(8a)-methyl octa(hexa)hydrocyclopenta[d][1,3]oxazines and [3,1]benzoxazines. J Am Chem Soc. 2003 Apr 16;125(15):4609-18. doi: 10.1021/ja021237t. PMID: 12683833.
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One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin. Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones.

The Journal of organic chemistry

Dang TT, Albrecht U, Gerwien K, Siebert M, Langer P.
PMID: 16526776
J Org Chem. 2006 Mar 17;71(6):2293-301. doi: 10.1021/jo052329e.

The one-pot cyclization of dilithiated oximes with epibromohydrin provided a convenient and regioselective approach to 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines. The reaction of the latter with phosphorus tribromide resulted in a Beckmann rearrangement and formation of 5-bromomethyl-2-iminotetrahydrofurans. The reaction of dilithiated hydrazones with...

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Dang TT, Albrecht U, Gerwien K, et al. One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin. Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones. J Org Chem. 2006;71(6):2293-301doi: 10.1021/jo052329e.
Dang, T. T., Albrecht, U., Gerwien, K., Siebert, M., & Langer, P. (2006). One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin. Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones. The Journal of organic chemistry, 71(6), 2293-301. https://doi.org/10.1021/jo052329e
Dang, Tuan Thanh, et al. "One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin. Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones." The Journal of organic chemistry vol. 71,6 (2006): 2293-301. doi: https://doi.org/10.1021/jo052329e
Dang TT, Albrecht U, Gerwien K, Siebert M, Langer P. One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin. Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones. J Org Chem. 2006 Mar 17;71(6):2293-301. doi: 10.1021/jo052329e. PMID: 16526776.
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Energy profiles for ketene cyclizations. Interconversion of 1,3-oxazin-6-ones, mesoionic 1,3-oxazinium olates and acylketenes, imidoylketenes, oxoketenimines, and cyclization products.

The Journal of organic chemistry

Bornemann H, Wentrup C.
PMID: 16018679
J Org Chem. 2005 Jul 22;70(15):5862-8. doi: 10.1021/jo050429e.

The energy surface connecting oxazinium olates 9, several possible conformers of ketenes 10 and 11, and the final cyclization products 12, 13 and 14, as well as the isomeric 1,3-oxazine-6-ones 15, ring opening of the latter to N-acylimidoylketenes 16,...

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Bornemann H, Wentrup C. Energy profiles for ketene cyclizations. Interconversion of 1,3-oxazin-6-ones, mesoionic 1,3-oxazinium olates and acylketenes, imidoylketenes, oxoketenimines, and cyclization products. J Org Chem. 2005;70(15):5862-8doi: 10.1021/jo050429e.
Bornemann, H., & Wentrup, C. (2005). Energy profiles for ketene cyclizations. Interconversion of 1,3-oxazin-6-ones, mesoionic 1,3-oxazinium olates and acylketenes, imidoylketenes, oxoketenimines, and cyclization products. The Journal of organic chemistry, 70(15), 5862-8. https://doi.org/10.1021/jo050429e
Bornemann, Holger, and Wentrup, Curt. "Energy profiles for ketene cyclizations. Interconversion of 1,3-oxazin-6-ones, mesoionic 1,3-oxazinium olates and acylketenes, imidoylketenes, oxoketenimines, and cyclization products." The Journal of organic chemistry vol. 70,15 (2005): 5862-8. doi: https://doi.org/10.1021/jo050429e
Bornemann H, Wentrup C. Energy profiles for ketene cyclizations. Interconversion of 1,3-oxazin-6-ones, mesoionic 1,3-oxazinium olates and acylketenes, imidoylketenes, oxoketenimines, and cyclization products. J Org Chem. 2005 Jul 22;70(15):5862-8. doi: 10.1021/jo050429e. PMID: 16018679.
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Fast and stable photochromic oxazines.

The Journal of organic chemistry

Tomasulo M, Sortino S, White AJ, Raymo FM.
PMID: 16277345
J Org Chem. 2005 Sep 30;70(20):8180-9. doi: 10.1021/jo051417w.

We have designed and synthesized two photochromic compounds incorporating fused indoline and benzooxazine fragments. Variable-temperature 1H NMR spectroscopy demonstrates that their central [1,3]oxazine ring opens thermally with free energy barriers ranging from 14 to 19 kcal mol(-1). The ring-opened...

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Tomasulo M, Sortino S, White AJ, et al. Fast and stable photochromic oxazines. J Org Chem. 2005;70(20):8180-9doi: 10.1021/jo051417w.
Tomasulo, M., Sortino, S., White, A. J., & Raymo, F. M. (2005). Fast and stable photochromic oxazines. The Journal of organic chemistry, 70(20), 8180-9. https://doi.org/10.1021/jo051417w
Tomasulo, Massimiliano, et al. "Fast and stable photochromic oxazines." The Journal of organic chemistry vol. 70,20 (2005): 8180-9. doi: https://doi.org/10.1021/jo051417w
Tomasulo M, Sortino S, White AJ, Raymo FM. Fast and stable photochromic oxazines. J Org Chem. 2005 Sep 30;70(20):8180-9. doi: 10.1021/jo051417w. PMID: 16277345.
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Mode selectivity in the intramolecular cyclization of ketenimines bearing N-acylimino units: a computational and experimental study.

The Journal of organic chemistry

Alajarín M, Sánchez-Andrada P, Vidal A, Tovar F.
PMID: 15704968
J Org Chem. 2005 Feb 18;70(4):1340-9. doi: 10.1021/jo0482716.

[reaction: see text] The mode selectivity in the intramolecular cyclization of a particular class of ketenimines bearing N-acylimino units has been studied by ab initio and DFT calculations. In the model compounds the carbonyl carbon atom and the keteniminic...

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Alajarín M, Sánchez-Andrada P, Vidal A, et al. Mode selectivity in the intramolecular cyclization of ketenimines bearing N-acylimino units: a computational and experimental study. J Org Chem. 2005;70(4):1340-9doi: 10.1021/jo0482716.
Alajarín, M., Sánchez-Andrada, P., Vidal, A., & Tovar, F. (2005). Mode selectivity in the intramolecular cyclization of ketenimines bearing N-acylimino units: a computational and experimental study. The Journal of organic chemistry, 70(4), 1340-9. https://doi.org/10.1021/jo0482716
Alajarín, Mateo, et al. "Mode selectivity in the intramolecular cyclization of ketenimines bearing N-acylimino units: a computational and experimental study." The Journal of organic chemistry vol. 70,4 (2005): 1340-9. doi: https://doi.org/10.1021/jo0482716
Alajarín M, Sánchez-Andrada P, Vidal A, Tovar F. Mode selectivity in the intramolecular cyclization of ketenimines bearing N-acylimino units: a computational and experimental study. J Org Chem. 2005 Feb 18;70(4):1340-9. doi: 10.1021/jo0482716. PMID: 15704968.
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Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines.

Chemistry (Weinheim an der Bergstrasse, Germany)

von Drathen T, Hoffmann F, Brasholz M.
PMID: 29750377
Chemistry. 2018 May 11; doi: 10.1002/chem.201801882. Epub 2018 May 11.

Few natural oxindole alkaloids possess an exceptional spiro-[(1,3)oxazinan-3,6'-oxindole] core structure, which results from an unusual oxidative indole rearrangement. The Rauvolfia alkaloid reserpine can be converted into the spirooxindole-1,3-oxazines dioxyreserpine and trioxyreserpine through efficient visible-light catalytic photooxygenation with anthraquinone photocatalysts....

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von Drathen T, Hoffmann F, Brasholz M. Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines. Chemistry. 2018;doi: 10.1002/chem.201801882.
von Drathen, T., Hoffmann, F., & Brasholz, M. (2018). Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines. Chemistry (Weinheim an der Bergstrasse, Germany), . https://doi.org/10.1002/chem.201801882
von Drathen, Thorsten, et al. "Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. (2018). doi: https://doi.org/10.1002/chem.201801882
von Drathen T, Hoffmann F, Brasholz M. Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines. Chemistry. 2018 May 11; doi: 10.1002/chem.201801882. Epub 2018 May 11. PMID: 29750377.
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Copper(i)/TF-BiphamPhos catalyzed asymmetric nitroso Diels-Alder reaction.

Chemical communications (Cambridge, England)

Li J, Tao HY, Wang CJ.
PMID: 28098270
Chem Commun (Camb). 2017 Feb 04;53(10):1657-1659. doi: 10.1039/c6cc09587a. Epub 2017 Jan 18.

A highly efficient enantioselective nitroso Diels-Alder reaction of 6-methyl-2-nitroso pyridine with various 1,3-dienes was successfully developed using a Cu(i)/(S)-TF-BiphamPhos complex as the catalyst. For most of the cyclic dienes, synthetically important heterocyclic 3,6-dihydro-1,2-oxazines were obtained in high yields with...

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Li J, Tao HY, Wang CJ. Copper(i)/TF-BiphamPhos catalyzed asymmetric nitroso Diels-Alder reaction. Chem Commun (Camb). 2017;53(10):1657-1659doi: 10.1039/c6cc09587a.
Li, J., Tao, H. Y., & Wang, C. J. (2017). Copper(i)/TF-BiphamPhos catalyzed asymmetric nitroso Diels-Alder reaction. Chemical communications (Cambridge, England), 53(10), 1657-1659. https://doi.org/10.1039/c6cc09587a
Li, Jun, et al. "Copper(i)/TF-BiphamPhos catalyzed asymmetric nitroso Diels-Alder reaction." Chemical communications (Cambridge, England) vol. 53,10 (2017): 1657-1659. doi: https://doi.org/10.1039/c6cc09587a
Li J, Tao HY, Wang CJ. Copper(i)/TF-BiphamPhos catalyzed asymmetric nitroso Diels-Alder reaction. Chem Commun (Camb). 2017 Feb 04;53(10):1657-1659. doi: 10.1039/c6cc09587a. Epub 2017 Jan 18. PMID: 28098270.
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