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Synthesis of zwitterionic compounds: fully saturated pyrimidinylium and 1,3-diazepinylium derivatives via the novel rearrangement of 3-oxobutanoic acid thioanilide derivatives.

The Journal of organic chemistry

Zaleska B, Bazanek T, Socha R, Karelus M, Grochowski J, Serda P.
PMID: 12076152
J Org Chem. 2002 Jun 28;67(13):4526-9. doi: 10.1021/jo025602a.

An unusual rearrangement following cyclization of 2-anilino-2-ethoxy-3-oxothiobutanoic acid with aliphatic 1,3- as well as 1,4-diamine leads to zwitterionic derivatives of 2-hydroxypropanoic acid. Moreover, with aromatic 1,2-diamines, fused heterocyclic systems such as pteridine, quinoxaline, and pyrido[2,3-b]pyrazine are obtained.

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Zaleska B, Bazanek T, Socha R, et al. Synthesis of zwitterionic compounds: fully saturated pyrimidinylium and 1,3-diazepinylium derivatives via the novel rearrangement of 3-oxobutanoic acid thioanilide derivatives. J Org Chem. 2002;67(13):4526-9doi: 10.1021/jo025602a.
Zaleska, B., Bazanek, T., Socha, R., Karelus, M., Grochowski, J., & Serda, P. (2002). Synthesis of zwitterionic compounds: fully saturated pyrimidinylium and 1,3-diazepinylium derivatives via the novel rearrangement of 3-oxobutanoic acid thioanilide derivatives. The Journal of organic chemistry, 67(13), 4526-9. https://doi.org/10.1021/jo025602a
Zaleska, Barbara, et al. "Synthesis of zwitterionic compounds: fully saturated pyrimidinylium and 1,3-diazepinylium derivatives via the novel rearrangement of 3-oxobutanoic acid thioanilide derivatives." The Journal of organic chemistry vol. 67,13 (2002): 4526-9. doi: https://doi.org/10.1021/jo025602a
Zaleska B, Bazanek T, Socha R, Karelus M, Grochowski J, Serda P. Synthesis of zwitterionic compounds: fully saturated pyrimidinylium and 1,3-diazepinylium derivatives via the novel rearrangement of 3-oxobutanoic acid thioanilide derivatives. J Org Chem. 2002 Jun 28;67(13):4526-9. doi: 10.1021/jo025602a. PMID: 12076152.
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Magnetostructural Correlations in Bis(&mgr;(2)-phenoxide)-Bridged Macrocyclic Dinuclear Copper(II) Complexes. Influence of Electron-Withdrawing Substituents on Exchange Coupling.

Inorganic chemistry

Thompson LK, Mandal SK, Tandon SS, Bridson JN, Park MK.
PMID: 11666507
Inorg Chem. 1996 May 22;35(11):3117-3125. doi: 10.1021/ic9514197.

Macrocyclic dicopper(II) complexes derived from 2,6-di(R)formylphenols and various linking diamines are surveyed and their magnetic and structural properties assessed. For those systems with "flat" dinuclear centers and no electronic perturbations associated with electron-withdrawing ligands or ligand groups, the complexes...

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Thompson LK, Mandal SK, Tandon SS, et al. Magnetostructural Correlations in Bis(&mgr;(2)-phenoxide)-Bridged Macrocyclic Dinuclear Copper(II) Complexes. Influence of Electron-Withdrawing Substituents on Exchange Coupling. Inorg Chem. 1996;35(11):3117-3125doi: 10.1021/ic9514197.
Thompson, L. K., Mandal, S. K., Tandon, S. S., Bridson, J. N., & Park, M. K. (1996). Magnetostructural Correlations in Bis(&mgr;(2)-phenoxide)-Bridged Macrocyclic Dinuclear Copper(II) Complexes. Influence of Electron-Withdrawing Substituents on Exchange Coupling. Inorganic chemistry, 35(11), 3117-3125. https://doi.org/10.1021/ic9514197
Thompson, Laurence K., et al. "Magnetostructural Correlations in Bis(&mgr;(2)-phenoxide)-Bridged Macrocyclic Dinuclear Copper(II) Complexes. Influence of Electron-Withdrawing Substituents on Exchange Coupling." Inorganic chemistry vol. 35,11 (1996): 3117-3125. doi: https://doi.org/10.1021/ic9514197
Thompson LK, Mandal SK, Tandon SS, Bridson JN, Park MK. Magnetostructural Correlations in Bis(&mgr;(2)-phenoxide)-Bridged Macrocyclic Dinuclear Copper(II) Complexes. Influence of Electron-Withdrawing Substituents on Exchange Coupling. Inorg Chem. 1996 May 22;35(11):3117-3125. doi: 10.1021/ic9514197. PMID: 11666507.
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Total Syntheses of (-)-Papuamine and (-)-Haliclonadiamine.

The Journal of organic chemistry

McDermott TS, Mortlock AA, Heathcock CH.
PMID: 11666993
J Org Chem. 1996 Jan 26;61(2):700-709. doi: 10.1021/jo951647i.

The pentacyclic marine alkaloids (-)-papuamine (1) and (-)-haliclonadiamine (2) have been prepared by total synthesis. The synthesis began with (-)-8, which was converted into diester 20 by way of bis-mesylate 17, dinitrile 18, and diacid 19. Dieckmann cyclization of...

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McDermott TS, Mortlock AA, Heathcock CH. Total Syntheses of (-)-Papuamine and (-)-Haliclonadiamine. J Org Chem. 1996;61(2):700-709doi: 10.1021/jo951647i.
McDermott, T. S., Mortlock, A. A., & Heathcock, C. H. (1996). Total Syntheses of (-)-Papuamine and (-)-Haliclonadiamine. The Journal of organic chemistry, 61(2), 700-709. https://doi.org/10.1021/jo951647i
McDermott, Todd S., et al. "Total Syntheses of (-)-Papuamine and (-)-Haliclonadiamine." The Journal of organic chemistry vol. 61,2 (1996): 700-709. doi: https://doi.org/10.1021/jo951647i
McDermott TS, Mortlock AA, Heathcock CH. Total Syntheses of (-)-Papuamine and (-)-Haliclonadiamine. J Org Chem. 1996 Jan 26;61(2):700-709. doi: 10.1021/jo951647i. PMID: 11666993.
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Synthesis of macrocyclic cage compounds by diamine-dihalide one-step coupling reaction.

The Journal of organic chemistry

Kon N, Takemura H, Otsuka K, Tanoue K, Nakashima S, Yasutake M, Tani K, Kimoto J, Shinmyozu T, Inazu T.
PMID: 10864755
J Org Chem. 2000 Jun 16;65(12):3708-15. doi: 10.1021/jo991911y.

Macropolycyclic cage compounds were synthesized by a direct reaction between diamines and bis(bromomethyl) compounds. The procedure for constructing the polycyclic cage structure is simple and straightforward. The macropolycyclic compounds obtainable from this cyclization procedure are three-dimensional cage compounds, and...

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Kon N, Takemura H, Otsuka K, et al. Synthesis of macrocyclic cage compounds by diamine-dihalide one-step coupling reaction. J Org Chem. 2000;65(12):3708-15doi: 10.1021/jo991911y.
Kon, N., Takemura, H., Otsuka, K., Tanoue, K., Nakashima, S., Yasutake, M., Tani, K., Kimoto, J., Shinmyozu, T., & Inazu, T. (2000). Synthesis of macrocyclic cage compounds by diamine-dihalide one-step coupling reaction. The Journal of organic chemistry, 65(12), 3708-15. https://doi.org/10.1021/jo991911y
Kon, et al. "Synthesis of macrocyclic cage compounds by diamine-dihalide one-step coupling reaction." The Journal of organic chemistry vol. 65,12 (2000): 3708-15. doi: https://doi.org/10.1021/jo991911y
Kon N, Takemura H, Otsuka K, Tanoue K, Nakashima S, Yasutake M, Tani K, Kimoto J, Shinmyozu T, Inazu T. Synthesis of macrocyclic cage compounds by diamine-dihalide one-step coupling reaction. J Org Chem. 2000 Jun 16;65(12):3708-15. doi: 10.1021/jo991911y. PMID: 10864755.
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Titanocene-Catalyzed Coupling of Amides in the Presence of Organosilanes To Form Vicinal Diamines This work was supported by the Natural Sciences and Engineering Research Council (Canada) and the Fonds FCAR du Québec. .

Angewandte Chemie (International ed. in English)

Selvakumar K, Harrod JF.
PMID: 11433467
Angew Chem Int Ed Engl. 2001 Jun 01;40(11):2129-2131.

No abstract available.

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Selvakumar K, Harrod JF. Titanocene-Catalyzed Coupling of Amides in the Presence of Organosilanes To Form Vicinal Diamines This work was supported by the Natural Sciences and Engineering Research Council (Canada) and the Fonds FCAR du Québec. . Angew Chem Int Ed Engl. 2001;40(11):2129-2131
Selvakumar, K., & Harrod, J. F. (2001). Titanocene-Catalyzed Coupling of Amides in the Presence of Organosilanes To Form Vicinal Diamines This work was supported by the Natural Sciences and Engineering Research Council (Canada) and the Fonds FCAR du Québec. . Angewandte Chemie (International ed. in English), 40(11), 2129-2131.
Selvakumar, Kumaravel, and Harrod, John F.. "Titanocene-Catalyzed Coupling of Amides in the Presence of Organosilanes To Form Vicinal Diamines This work was supported by the Natural Sciences and Engineering Research Council (Canada) and the Fonds FCAR du Québec. ." Angewandte Chemie (International ed. in English) vol. 40,11 (2001): 2129-2131.
Selvakumar K, Harrod JF. Titanocene-Catalyzed Coupling of Amides in the Presence of Organosilanes To Form Vicinal Diamines This work was supported by the Natural Sciences and Engineering Research Council (Canada) and the Fonds FCAR du Québec. . Angew Chem Int Ed Engl. 2001 Jun 01;40(11):2129-2131. PMID: 11433467.
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Compartmental Schiff-base ligands as selective double-loaded extractants for copper(II).

Chemical communications (Cambridge, England)

Black D, Blake AJ, Finn RL, Lindoy LF, Nezhadali A, Rougnaghi G, Tasker PA, Schröder M.
PMID: 12120064
Chem Commun (Camb). 2002 Feb 21;(4):340-1. doi: 10.1039/b109635b.

The Robson compartmental macrocyclic ligand derived from the condensation of derivatives of 2,6-diformylphenol and diamines has been prepared for the first time in its free ligand form; competitive three-phase transport and two-phase extraction studies confirm high double-loaded selectivity for...

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Black D, Blake AJ, Finn RL, et al. Compartmental Schiff-base ligands as selective double-loaded extractants for copper(II). Chem Commun (Camb). 2002;(4):340-1doi: 10.1039/b109635b.
Black, D., Blake, A. J., Finn, R. L., Lindoy, L. F., Nezhadali, A., Rougnaghi, G., Tasker, P. A., & Schröder, M. (2002). Compartmental Schiff-base ligands as selective double-loaded extractants for copper(II). Chemical communications (Cambridge, England), (4), 340-1. https://doi.org/10.1039/b109635b
Black, Daniel, et al. "Compartmental Schiff-base ligands as selective double-loaded extractants for copper(II)." Chemical communications (Cambridge, England) vol. ,4 (2002): 340-1. doi: https://doi.org/10.1039/b109635b
Black D, Blake AJ, Finn RL, Lindoy LF, Nezhadali A, Rougnaghi G, Tasker PA, Schröder M. Compartmental Schiff-base ligands as selective double-loaded extractants for copper(II). Chem Commun (Camb). 2002 Feb 21;(4):340-1. doi: 10.1039/b109635b. PMID: 12120064.
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Substituted Isoquinolines by Noyori Transfer Hydrogenation: Enantioselective Synthesis of Chiral Diamines Containing an Aniline Subunit.

The Journal of organic chemistry

Vedejs E, Trapencieris P, Suna E.
PMID: 11674678
J Org Chem. 1999 Sep 03;64(18):6724-6729. doi: 10.1021/jo990594s.

Transfer hydrogenation using the Noyori catalyst 5-Ts is effective for the enantioselective hydrogenation of imines containing fully substituted nitrogen groups (12 or 13). Analogues such as 11c could not be reduced in practical yield, apparently due to product inhibition...

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Vedejs E, Trapencieris P, Suna E. Substituted Isoquinolines by Noyori Transfer Hydrogenation: Enantioselective Synthesis of Chiral Diamines Containing an Aniline Subunit. J Org Chem. 1999;64(18):6724-6729doi: 10.1021/jo990594s.
Vedejs, E., Trapencieris, P., & Suna, E. (1999). Substituted Isoquinolines by Noyori Transfer Hydrogenation: Enantioselective Synthesis of Chiral Diamines Containing an Aniline Subunit. The Journal of organic chemistry, 64(18), 6724-6729. https://doi.org/10.1021/jo990594s
Vedejs, E., et al. "Substituted Isoquinolines by Noyori Transfer Hydrogenation: Enantioselective Synthesis of Chiral Diamines Containing an Aniline Subunit." The Journal of organic chemistry vol. 64,18 (1999): 6724-6729. doi: https://doi.org/10.1021/jo990594s
Vedejs E, Trapencieris P, Suna E. Substituted Isoquinolines by Noyori Transfer Hydrogenation: Enantioselective Synthesis of Chiral Diamines Containing an Aniline Subunit. J Org Chem. 1999 Sep 03;64(18):6724-6729. doi: 10.1021/jo990594s. PMID: 11674678.
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Synthesis of 1,4-diazines by ring expansion of 1,3-diazines.

The Journal of organic chemistry

Zaleska B, Socha R, Karelus M, Szneler E, Grochowski J, Serda P.
PMID: 12636399
J Org Chem. 2003 Mar 21;68(6):2334-7. doi: 10.1021/jo026756t.

Fully saturated piperazin-3-one and quinoxalin-3-one derivatives were prepared by reactions of 2-anilino-2-ethoxy-3-oxothiobutanoic acid anilide with aliphatic 1,2-diamines. An unusual ring expansion of the intermediate 1,3-diazines leads to 1,4-diazines. Moreover, quinoxalin-3-one derivatives from chiral trans-1,2-diaminocyclohexane were obtained with diastereoselectivity >95%.

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Zaleska B, Socha R, Karelus M, et al. Synthesis of 1,4-diazines by ring expansion of 1,3-diazines. J Org Chem. 2003;68(6):2334-7doi: 10.1021/jo026756t.
Zaleska, B., Socha, R., Karelus, M., Szneler, E., Grochowski, J., & Serda, P. (2003). Synthesis of 1,4-diazines by ring expansion of 1,3-diazines. The Journal of organic chemistry, 68(6), 2334-7. https://doi.org/10.1021/jo026756t
Zaleska, Barbara, et al. "Synthesis of 1,4-diazines by ring expansion of 1,3-diazines." The Journal of organic chemistry vol. 68,6 (2003): 2334-7. doi: https://doi.org/10.1021/jo026756t
Zaleska B, Socha R, Karelus M, Szneler E, Grochowski J, Serda P. Synthesis of 1,4-diazines by ring expansion of 1,3-diazines. J Org Chem. 2003 Mar 21;68(6):2334-7. doi: 10.1021/jo026756t. PMID: 12636399.
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Hydrated salts of 3,5-dihydroxybenzoic acid with organic diamines: hydrogen-bonded supramolecular structures in two and three dimensions.

Acta crystallographica. Section B, Structural science

Burchell CJ, Ferguson G, Lough AJ, Gregson RM, Glidewell C.
PMID: 11373391
Acta Crystallogr B. 2001 Jun;57:329-38. doi: 10.1107/s0108768100019832. Epub 2001 Jun 01.

The trigonally trisubstituted acid 3,5-dihydroxybenzoic acid forms hydrated salt-type adducts with organic diamines. In 1,4-diazabicyclo[2.2.2]octane-3,5-dihydroxybenzoic acid-water (1/1/1) (1), where Z' = 2 in P2(1)/c, the constitution is [HN(CH(2)CH(2))(3)N](+).[(HO)(2)C(6)H(3)COO](-).H(2)O: the anions and the water molecules are linked by six O-H.O...

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Burchell CJ, Ferguson G, Lough AJ, et al. Hydrated salts of 3,5-dihydroxybenzoic acid with organic diamines: hydrogen-bonded supramolecular structures in two and three dimensions. Acta Crystallogr B. 2001;57:329-38doi: 10.1107/s0108768100019832.
Burchell, C. J., Ferguson, G., Lough, A. J., Gregson, R. M., & Glidewell, C. (2001). Hydrated salts of 3,5-dihydroxybenzoic acid with organic diamines: hydrogen-bonded supramolecular structures in two and three dimensions. Acta crystallographica. Section B, Structural science, 57329-38. https://doi.org/10.1107/s0108768100019832
Burchell, C J, et al. "Hydrated salts of 3,5-dihydroxybenzoic acid with organic diamines: hydrogen-bonded supramolecular structures in two and three dimensions." Acta crystallographica. Section B, Structural science vol. 57 (2001): 329-38. doi: https://doi.org/10.1107/s0108768100019832
Burchell CJ, Ferguson G, Lough AJ, Gregson RM, Glidewell C. Hydrated salts of 3,5-dihydroxybenzoic acid with organic diamines: hydrogen-bonded supramolecular structures in two and three dimensions. Acta Crystallogr B. 2001 Jun;57:329-38. doi: 10.1107/s0108768100019832. Epub 2001 Jun 01. PMID: 11373391.
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Organic chloramine analysis and free chlorine quantification by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry.

Analytical chemistry

Takats Z, Koch KJ, Cooks RG.
PMID: 11575802
Anal Chem. 2001 Sep 15;73(18):4522-9. doi: 10.1021/ac010338r.

Atmospheric pressure chemical ionization (APCI) and electrospray ionization (ESI), together with tandem mass spectrometry (MSn), are used to study the mechanism of chlorination of amines and to develop a method for qualitative and quantitative determination of organic chloramines. Cyclohexylamine...

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Takats Z, Koch KJ, Cooks RG. Organic chloramine analysis and free chlorine quantification by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry. Anal Chem. 2001;73(18):4522-9doi: 10.1021/ac010338r.
Takats, Z., Koch, K. J., & Cooks, R. G. (2001). Organic chloramine analysis and free chlorine quantification by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry. Analytical chemistry, 73(18), 4522-9. https://doi.org/10.1021/ac010338r
Takats, Z, et al. "Organic chloramine analysis and free chlorine quantification by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry." Analytical chemistry vol. 73,18 (2001): 4522-9. doi: https://doi.org/10.1021/ac010338r
Takats Z, Koch KJ, Cooks RG. Organic chloramine analysis and free chlorine quantification by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry. Anal Chem. 2001 Sep 15;73(18):4522-9. doi: 10.1021/ac010338r. PMID: 11575802.
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Phosphonopropionic acid as a building block in supramolecular chemistry: salts with organic diamines.

Acta crystallographica. Section B, Structural science

Bowes KF, Ferguson G, Lough AJ, Glidewell C.
PMID: 12657817
Acta Crystallogr B. 2003 Apr;59:248-62. doi: 10.1107/s0108768102021237. Epub 2003 Mar 26.

The structures of seven salts formed by phosphonopropionic acid with organic diamines are reported; in these salts, the hydrogen-bonded substructures formed by the anions can be zero-, one- or two-dimensional, while the overall hydrogen-bonded supramolecular structures are three-dimensional. The...

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Bowes KF, Ferguson G, Lough AJ, et al. Phosphonopropionic acid as a building block in supramolecular chemistry: salts with organic diamines. Acta Crystallogr B. 2003;59:248-62doi: 10.1107/s0108768102021237.
Bowes, K. F., Ferguson, G., Lough, A. J., & Glidewell, C. (2003). Phosphonopropionic acid as a building block in supramolecular chemistry: salts with organic diamines. Acta crystallographica. Section B, Structural science, 59248-62. https://doi.org/10.1107/s0108768102021237
Bowes, Katharine F, et al. "Phosphonopropionic acid as a building block in supramolecular chemistry: salts with organic diamines." Acta crystallographica. Section B, Structural science vol. 59 (2003): 248-62. doi: https://doi.org/10.1107/s0108768102021237
Bowes KF, Ferguson G, Lough AJ, Glidewell C. Phosphonopropionic acid as a building block in supramolecular chemistry: salts with organic diamines. Acta Crystallogr B. 2003 Apr;59:248-62. doi: 10.1107/s0108768102021237. Epub 2003 Mar 26. PMID: 12657817.
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Clays as a host matrix in the synthesis of organic macrocycles.

Chemistry (Weinheim an der Bergstrasse, Germany)

Georgakilas V, Gournis D, Bourlinos AB, Karakassides MA, Petridis D.
PMID: 12916116
Chemistry. 2003 Aug 18;9(16):3904-8. doi: 10.1002/chem.200204555.

A new approach for the synthesis of amide macrocycles, based on the use of organo-clay derivatives as controlling template, is proposed as an alternative to the rotaxane method. Dications of p-xylylene diamine inserted in the clay interlayer space act...

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Georgakilas V, Gournis D, Bourlinos AB, et al. Clays as a host matrix in the synthesis of organic macrocycles. Chemistry. 2003;9(16):3904-8doi: 10.1002/chem.200204555.
Georgakilas, V., Gournis, D., Bourlinos, A. B., Karakassides, M. A., & Petridis, D. (2003). Clays as a host matrix in the synthesis of organic macrocycles. Chemistry (Weinheim an der Bergstrasse, Germany), 9(16), 3904-8. https://doi.org/10.1002/chem.200204555
Georgakilas, Vasilios, et al. "Clays as a host matrix in the synthesis of organic macrocycles." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 9,16 (2003): 3904-8. doi: https://doi.org/10.1002/chem.200204555
Georgakilas V, Gournis D, Bourlinos AB, Karakassides MA, Petridis D. Clays as a host matrix in the synthesis of organic macrocycles. Chemistry. 2003 Aug 18;9(16):3904-8. doi: 10.1002/chem.200204555. PMID: 12916116.
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Showing 25 to 36 of 915 entries