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Three-component homo 3 + 2 dipolar cycloaddition. A diversity-oriented synthesis of tetrahydro-1,2-oxazines and FR900482 skeletal congeners.

Organic letters

Young IS, Kerr MA.
PMID: 14703370
Org Lett. 2004 Jan 08;6(1):139-41. doi: 10.1021/ol0362919.

[reaction: see text] The reaction of nitrones, formed in situ by reaction of hydroxylamines with aldehydes, with 1,1-cyclopropanediesters results in the formation of tetrahydro-1,2-oxazines via a homo 3 + 2 dipolar cycloaddition. This three-component coupling allows for the formation...

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Young IS, Kerr MA. Three-component homo 3 + 2 dipolar cycloaddition. A diversity-oriented synthesis of tetrahydro-1,2-oxazines and FR900482 skeletal congeners. Org Lett. 2004;6(1):139-41doi: 10.1021/ol0362919.
Young, I. S., & Kerr, M. A. (2004). Three-component homo 3 + 2 dipolar cycloaddition. A diversity-oriented synthesis of tetrahydro-1,2-oxazines and FR900482 skeletal congeners. Organic letters, 6(1), 139-41. https://doi.org/10.1021/ol0362919
Young, Ian S, and Kerr, Michael A. "Three-component homo 3 + 2 dipolar cycloaddition. A diversity-oriented synthesis of tetrahydro-1,2-oxazines and FR900482 skeletal congeners." Organic letters vol. 6,1 (2004): 139-41. doi: https://doi.org/10.1021/ol0362919
Young IS, Kerr MA. Three-component homo 3 + 2 dipolar cycloaddition. A diversity-oriented synthesis of tetrahydro-1,2-oxazines and FR900482 skeletal congeners. Org Lett. 2004 Jan 08;6(1):139-41. doi: 10.1021/ol0362919. PMID: 14703370.
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Discovery of C-3 Tethered 2-oxo-benzo[1,4]oxazines as Potent Antioxidants: Bio-Inspired Based Design, Synthesis, Biological Evaluation, Cytotoxic, and .

Frontiers in chemistry

Sharma V, Jaiswal PK, Saran M, Yadav DK, Saloni, Mathur M, Swami AK, Misra S, Kim MH, Chaudhary S.
PMID: 29629369
Front Chem. 2018 Mar 23;6:56. doi: 10.3389/fchem.2018.00056. eCollection 2018.

The discovery of C-3 tethered 2-oxo-benzo[1,4]oxazines as potent antioxidants is disclosed. All the analogs

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Sharma V, Jaiswal PK, Saran M, et al. Discovery of C-3 Tethered 2-oxo-benzo[1,4]oxazines as Potent Antioxidants: Bio-Inspired Based Design, Synthesis, Biological Evaluation, Cytotoxic, and . Front Chem. 2018;6:56doi: 10.3389/fchem.2018.00056.
Sharma, V., Jaiswal, P. K., Saran, M., Yadav, D. K., Saloni, Mathur, M., Swami, A. K., Misra, S., Kim, M. H., & Chaudhary, S. (2018). Discovery of C-3 Tethered 2-oxo-benzo[1,4]oxazines as Potent Antioxidants: Bio-Inspired Based Design, Synthesis, Biological Evaluation, Cytotoxic, and . Frontiers in chemistry, 656. https://doi.org/10.3389/fchem.2018.00056
Sharma, Vashundhra, et al. "Discovery of C-3 Tethered 2-oxo-benzo[1,4]oxazines as Potent Antioxidants: Bio-Inspired Based Design, Synthesis, Biological Evaluation, Cytotoxic, and ." Frontiers in chemistry vol. 6 (2018): 56. doi: https://doi.org/10.3389/fchem.2018.00056
Sharma V, Jaiswal PK, Saran M, Yadav DK, Saloni, Mathur M, Swami AK, Misra S, Kim MH, Chaudhary S. Discovery of C-3 Tethered 2-oxo-benzo[1,4]oxazines as Potent Antioxidants: Bio-Inspired Based Design, Synthesis, Biological Evaluation, Cytotoxic, and . Front Chem. 2018 Mar 23;6:56. doi: 10.3389/fchem.2018.00056. eCollection 2018. PMID: 29629369; PMCID: PMC5876303.
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Identification of a novel 1,2 oxazine that can induce apoptosis by targeting NF-κB in hepatocellular carcinoma cells.

Biotechnology reports (Amsterdam, Netherlands)

Somu C, Mohan CD, Ambekar S, Dukanya, Rangappa S, Baburajeev CP, Sukhorukov A, Mishra S, Shanmugam MK, Chinnathambi A, Awad Alahmadi T, Alharbi SA, Basappa, Rangappa KS.
PMID: 32140443
Biotechnol Rep (Amst). 2020 Feb 19;25:e00438. doi: 10.1016/j.btre.2020.e00438. eCollection 2020 Mar.

Constitutive activation of NF-κB is associated with proinflammatory diseases and suppression of the NF-κB signaling pathway has been considered as an effective therapeutic strategy in the treatment of various cancers including hepatocellular carcinoma (HCC). Herein, we report the synthesis...

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Somu C, Mohan CD, Ambekar S, et al. Identification of a novel 1,2 oxazine that can induce apoptosis by targeting NF-κB in hepatocellular carcinoma cells. Biotechnol Rep (Amst). 2020;25:e00438doi: 10.1016/j.btre.2020.e00438.
Somu, C., Mohan, C. D., Ambekar, S., Dukanya, Rangappa, S., Baburajeev, C. P., Sukhorukov, A., Mishra, S., Shanmugam, M. K., Chinnathambi, A., Awad Alahmadi, T., Alharbi, S. A., Basappa, & Rangappa, K. S. (2020). Identification of a novel 1,2 oxazine that can induce apoptosis by targeting NF-κB in hepatocellular carcinoma cells. Biotechnology reports (Amsterdam, Netherlands), 25e00438. https://doi.org/10.1016/j.btre.2020.e00438
Somu, Chaithanya, et al. "Identification of a novel 1,2 oxazine that can induce apoptosis by targeting NF-κB in hepatocellular carcinoma cells." Biotechnology reports (Amsterdam, Netherlands) vol. 25 (2020): e00438. doi: https://doi.org/10.1016/j.btre.2020.e00438
Somu C, Mohan CD, Ambekar S, Dukanya, Rangappa S, Baburajeev CP, Sukhorukov A, Mishra S, Shanmugam MK, Chinnathambi A, Awad Alahmadi T, Alharbi SA, Basappa, Rangappa KS. Identification of a novel 1,2 oxazine that can induce apoptosis by targeting NF-κB in hepatocellular carcinoma cells. Biotechnol Rep (Amst). 2020 Feb 19;25:e00438. doi: 10.1016/j.btre.2020.e00438. eCollection 2020 Mar. PMID: 32140443; PMCID: PMC7044713.
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A Catalytic Enantioselective Iodocyclization Route to Dihydrooxazines.

Organic letters

Suresh R, Simlandy AK, Mukherjee S.
PMID: 29431444
Org Lett. 2018 Mar 02;20(5):1300-1303. doi: 10.1021/acs.orglett.8b00002. Epub 2018 Feb 12.

The first catalytic enantioselective synthesis of 5,6-dihydro-4H-1,2-oxazines bearing an oxygen-containing quaternary stereogenic center has been developed through iodoetherification of γ,δ-unsaturated oximes. This operationally straightforward reaction is catalyzed by Cinchona alkaloids-based bifunctional tertiary aminothiourea derivatives and furnishes the products generally...

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Suresh R, Simlandy AK, Mukherjee S. A Catalytic Enantioselective Iodocyclization Route to Dihydrooxazines. Org Lett. 2018;20(5):1300-1303doi: 10.1021/acs.orglett.8b00002.
Suresh, R., Simlandy, A. K., & Mukherjee, S. (2018). A Catalytic Enantioselective Iodocyclization Route to Dihydrooxazines. Organic letters, 20(5), 1300-1303. https://doi.org/10.1021/acs.orglett.8b00002
Suresh, Rahul, et al. "A Catalytic Enantioselective Iodocyclization Route to Dihydrooxazines." Organic letters vol. 20,5 (2018): 1300-1303. doi: https://doi.org/10.1021/acs.orglett.8b00002
Suresh R, Simlandy AK, Mukherjee S. A Catalytic Enantioselective Iodocyclization Route to Dihydrooxazines. Org Lett. 2018 Mar 02;20(5):1300-1303. doi: 10.1021/acs.orglett.8b00002. Epub 2018 Feb 12. PMID: 29431444.
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Silyl Group-Directed 6-exo-dig Iodocyclization of Homopropargylic Carbamates and Amides.

Chemistry (Weinheim an der Bergstrasse, Germany)

Okitsu T, Nakahigashi H, Sugihara R, Fukuda I, Tsuji S, In Y, Wada A.
PMID: 30311697
Chemistry. 2018 Dec 12;24(70):18638-18642. doi: 10.1002/chem.201804794. Epub 2018 Nov 26.

Iodocyclization of silyl group-substituted homopropargylic carbamates and amides proceeded via 6-exo-dig mode to afford 6-vinylene-4,5-dihydro-1,3-oxazines in moderate to quantitative yields. This is the first report for silyl group-solely directed iodocyclization of alkynes utilizing the β-silyl effect. Under these mild...

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Okitsu T, Nakahigashi H, Sugihara R, et al. Silyl Group-Directed 6-exo-dig Iodocyclization of Homopropargylic Carbamates and Amides. Chemistry. 2018;24(70):18638-18642doi: 10.1002/chem.201804794.
Okitsu, T., Nakahigashi, H., Sugihara, R., Fukuda, I., Tsuji, S., In, Y., & Wada, A. (2018). Silyl Group-Directed 6-exo-dig Iodocyclization of Homopropargylic Carbamates and Amides. Chemistry (Weinheim an der Bergstrasse, Germany), 24(70), 18638-18642. https://doi.org/10.1002/chem.201804794
Okitsu, Takashi, et al. "Silyl Group-Directed 6-exo-dig Iodocyclization of Homopropargylic Carbamates and Amides." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 24,70 (2018): 18638-18642. doi: https://doi.org/10.1002/chem.201804794
Okitsu T, Nakahigashi H, Sugihara R, Fukuda I, Tsuji S, In Y, Wada A. Silyl Group-Directed 6-exo-dig Iodocyclization of Homopropargylic Carbamates and Amides. Chemistry. 2018 Dec 12;24(70):18638-18642. doi: 10.1002/chem.201804794. Epub 2018 Nov 26. PMID: 30311697.
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Structural diversity through gold catalysis: stereoselective synthesis of N-hydroxypyrrolines, dihydroisoxazoles, and dihydro-1,2-oxazines.

Angewandte Chemie (International ed. in English)

Winter C, Krause N.
PMID: 19606437
Angew Chem Int Ed Engl. 2009;48(34):6339-42. doi: 10.1002/anie.200902355.

No abstract available.

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Winter C, Krause N. Structural diversity through gold catalysis: stereoselective synthesis of N-hydroxypyrrolines, dihydroisoxazoles, and dihydro-1,2-oxazines. Angew Chem Int Ed Engl. 2009;48(34):6339-42doi: 10.1002/anie.200902355.
Winter, C., & Krause, N. (2009). Structural diversity through gold catalysis: stereoselective synthesis of N-hydroxypyrrolines, dihydroisoxazoles, and dihydro-1,2-oxazines. Angewandte Chemie (International ed. in English), 48(34), 6339-42. https://doi.org/10.1002/anie.200902355
Winter, Christian, and Krause, Norbert. "Structural diversity through gold catalysis: stereoselective synthesis of N-hydroxypyrrolines, dihydroisoxazoles, and dihydro-1,2-oxazines." Angewandte Chemie (International ed. in English) vol. 48,34 (2009): 6339-42. doi: https://doi.org/10.1002/anie.200902355
Winter C, Krause N. Structural diversity through gold catalysis: stereoselective synthesis of N-hydroxypyrrolines, dihydroisoxazoles, and dihydro-1,2-oxazines. Angew Chem Int Ed Engl. 2009;48(34):6339-42. doi: 10.1002/anie.200902355. PMID: 19606437.
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Resin-bound 4H-1,3-oxazine-masked beta-diketones for functionalizing cleavage strategy.

Journal of combinatorial chemistry

Vanier C, Wagner A, Mioskowski C.
PMID: 15360222
J Comb Chem. 2004 Sep-Oct;6(5):846-50. doi: 10.1021/cc030109d.

Resin-bound 4H-1,3-oxazines are synthesized by the stepwise condensation of an amide resin, an aldehyde, and an alkyne. Upon DDQ activation, oxazines are converted into oxazinium salts. When treated with hydrazines, these resin-bound beta-diketone equivalents yield pyrazoles through a functionalizing...

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Vanier C, Wagner A, Mioskowski C. Resin-bound 4H-1,3-oxazine-masked beta-diketones for functionalizing cleavage strategy. J Comb Chem. 2004;6(5):846-50doi: 10.1021/cc030109d.
Vanier, C., Wagner, A., & Mioskowski, C. (2004). Resin-bound 4H-1,3-oxazine-masked beta-diketones for functionalizing cleavage strategy. Journal of combinatorial chemistry, 6(5), 846-50. https://doi.org/10.1021/cc030109d
Vanier, Cécile, et al. "Resin-bound 4H-1,3-oxazine-masked beta-diketones for functionalizing cleavage strategy." Journal of combinatorial chemistry vol. 6,5 (2004): 846-50. doi: https://doi.org/10.1021/cc030109d
Vanier C, Wagner A, Mioskowski C. Resin-bound 4H-1,3-oxazine-masked beta-diketones for functionalizing cleavage strategy. J Comb Chem. 2004 Sep-Oct;6(5):846-50. doi: 10.1021/cc030109d. PMID: 15360222.
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The first catalytic inverse-electron demand hetero-Diels-Alder reaction of nitroso alkenes using pyrrolidine as an organocatalyst.

Organic & biomolecular chemistry

Wabnitz TC, Saaby S, Jørgensen KA.
PMID: 15007410
Org Biomol Chem. 2004 Mar 21;2(6):828-34. doi: 10.1039/b316518c. Epub 2004 Feb 16.

The first catalytic inverse-electron demand hetero-Diels-Alder reaction of nitroso alkenes has been developed. Nitroso alkenes were generated in situ from alpha-halooximes and underwent [4 + 2]-cycloadditions with enamines as dienophiles formed from aldehydes and pyrrolidine (10 mol%) as an...

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Wabnitz TC, Saaby S, Jørgensen KA. The first catalytic inverse-electron demand hetero-Diels-Alder reaction of nitroso alkenes using pyrrolidine as an organocatalyst. Org Biomol Chem. 2004;2(6):828-34doi: 10.1039/b316518c.
Wabnitz, T. C., Saaby, S., & Jørgensen, K. A. (2004). The first catalytic inverse-electron demand hetero-Diels-Alder reaction of nitroso alkenes using pyrrolidine as an organocatalyst. Organic & biomolecular chemistry, 2(6), 828-34. https://doi.org/10.1039/b316518c
Wabnitz, Tobias C, et al. "The first catalytic inverse-electron demand hetero-Diels-Alder reaction of nitroso alkenes using pyrrolidine as an organocatalyst." Organic & biomolecular chemistry vol. 2,6 (2004): 828-34. doi: https://doi.org/10.1039/b316518c
Wabnitz TC, Saaby S, Jørgensen KA. The first catalytic inverse-electron demand hetero-Diels-Alder reaction of nitroso alkenes using pyrrolidine as an organocatalyst. Org Biomol Chem. 2004 Mar 21;2(6):828-34. doi: 10.1039/b316518c. Epub 2004 Feb 16. PMID: 15007410.
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Chromogenic oxazines for cyanide detection.

The Journal of organic chemistry

Tomasulo M, Sortino S, White AJ, Raymo FM.
PMID: 16408989
J Org Chem. 2006 Jan 20;71(2):744-53. doi: 10.1021/jo052096r.

[reaction: see text] We have designed two heterocyclic compounds for the colorimetric detection of cyanide. The skeleton of both molecules fuses a benzooxazine ring to an indoline fragment and can be assembled efficiently in three synthetic steps starting from...

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Tomasulo M, Sortino S, White AJ, et al. Chromogenic oxazines for cyanide detection. J Org Chem. 2006;71(2):744-53doi: 10.1021/jo052096r.
Tomasulo, M., Sortino, S., White, A. J., & Raymo, F. M. (2006). Chromogenic oxazines for cyanide detection. The Journal of organic chemistry, 71(2), 744-53. https://doi.org/10.1021/jo052096r
Tomasulo, Massimiliano, et al. "Chromogenic oxazines for cyanide detection." The Journal of organic chemistry vol. 71,2 (2006): 744-53. doi: https://doi.org/10.1021/jo052096r
Tomasulo M, Sortino S, White AJ, Raymo FM. Chromogenic oxazines for cyanide detection. J Org Chem. 2006 Jan 20;71(2):744-53. doi: 10.1021/jo052096r. PMID: 16408989.
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The [4+2] cycloaddition of donor-acceptor cyclobutanes and nitrosoarenes.

Chemical communications (Cambridge, England)

Vemula N, Stevens AC, Schon TB, Pagenkopf BL.
PMID: 24389976
Chem Commun (Camb). 2014 Feb 18;50(14):1668-70. doi: 10.1039/c3cc47775d. Epub 2014 Jan 06.

The Yb(OTf)3 catalyzed [4+2] cycloaddition between donor-acceptor cyclobutanes and nitrosoarenes is disclosed. This method facilitates the synthesis of tetrahydro-1,2-oxazines in good to excellent yields as single diastereomers. Except for a few electron-deficient nitrosoarenes, excellent regioselectivity was observed throughout these...

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Vemula N, Stevens AC, Schon TB, et al. The [4+2] cycloaddition of donor-acceptor cyclobutanes and nitrosoarenes. Chem Commun (Camb). 2014;50(14):1668-70doi: 10.1039/c3cc47775d.
Vemula, N., Stevens, A. C., Schon, T. B., & Pagenkopf, B. L. (2014). The [4+2] cycloaddition of donor-acceptor cyclobutanes and nitrosoarenes. Chemical communications (Cambridge, England), 50(14), 1668-70. https://doi.org/10.1039/c3cc47775d
Vemula, Naresh, et al. "The [4+2] cycloaddition of donor-acceptor cyclobutanes and nitrosoarenes." Chemical communications (Cambridge, England) vol. 50,14 (2014): 1668-70. doi: https://doi.org/10.1039/c3cc47775d
Vemula N, Stevens AC, Schon TB, Pagenkopf BL. The [4+2] cycloaddition of donor-acceptor cyclobutanes and nitrosoarenes. Chem Commun (Camb). 2014 Feb 18;50(14):1668-70. doi: 10.1039/c3cc47775d. Epub 2014 Jan 06. PMID: 24389976.
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Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity.

The Journal of organic chemistry

Karadeolian A, Kerr MA.
PMID: 17999536
J Org Chem. 2007 Dec 21;72(26):10251-3. doi: 10.1021/jo702073w. Epub 2007 Nov 14.

The reaction of 2,3-disubstituted-1,1-cyclopropanediesters with nitrones under Lewis acid conditions produces tetrahydro-1,2-oxazines in which the cis/trans relationship of the cyclopropanes is not conserved. Reacting nitrones with 2,3-cis-disubstituted cyclopropanes lead to 5,6-trans-oxazines, and 2,3-trans-disubstituted cyclopropanes lead to 5,6-cis-oxazines. This observed...

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Karadeolian A, Kerr MA. Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity. J Org Chem. 2007;72(26):10251-3doi: 10.1021/jo702073w.
Karadeolian, A., & Kerr, M. A. (2007). Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity. The Journal of organic chemistry, 72(26), 10251-3. https://doi.org/10.1021/jo702073w
Karadeolian, Avedis, and Kerr, Michael A. "Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity." The Journal of organic chemistry vol. 72,26 (2007): 10251-3. doi: https://doi.org/10.1021/jo702073w
Karadeolian A, Kerr MA. Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity. J Org Chem. 2007 Dec 21;72(26):10251-3. doi: 10.1021/jo702073w. Epub 2007 Nov 14. PMID: 17999536.
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Effects of N-substitution on the fragmentations of some cyclohexene-fused 2-N-phenyliminoperhydro-3,1-oxazines and related thiazines.

Journal of the American Society for Mass Spectrometry

Vainiotalo P, Partanen T, Fülöp F, Bernáth G, Pihlaja K.
PMID: 24242172
J Am Soc Mass Spectrom. 1991 Apr;2(2):125-9. doi: 10.1016/1044-0305(91)80006-S.

Six cyclohexene-fused 2-N-phenyliminoperhydro-3,1-oxazines and four related thiazines were prepared and their mass spectrometric behavior was studied by means of metastable ion analysis and exact mass measurement. In most of the fragmentations, extensive rearrangements took place. The decompositions through the...

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Vainiotalo P, Partanen T, Fülöp F, et al. Effects of N-substitution on the fragmentations of some cyclohexene-fused 2-N-phenyliminoperhydro-3,1-oxazines and related thiazines. J Am Soc Mass Spectrom. 1991;2(2):125-9doi: 10.1016/1044-0305(91)80006-S.
Vainiotalo, P., Partanen, T., Fülöp, F., Bernáth, G., & Pihlaja, K. (1991). Effects of N-substitution on the fragmentations of some cyclohexene-fused 2-N-phenyliminoperhydro-3,1-oxazines and related thiazines. Journal of the American Society for Mass Spectrometry, 2(2), 125-9. https://doi.org/10.1016/1044-0305(91)80006-S
Vainiotalo, P, et al. "Effects of N-substitution on the fragmentations of some cyclohexene-fused 2-N-phenyliminoperhydro-3,1-oxazines and related thiazines." Journal of the American Society for Mass Spectrometry vol. 2,2 (1991): 125-9. doi: https://doi.org/10.1016/1044-0305(91)80006-S
Vainiotalo P, Partanen T, Fülöp F, Bernáth G, Pihlaja K. Effects of N-substitution on the fragmentations of some cyclohexene-fused 2-N-phenyliminoperhydro-3,1-oxazines and related thiazines. J Am Soc Mass Spectrom. 1991 Apr;2(2):125-9. doi: 10.1016/1044-0305(91)80006-S. PMID: 24242172.
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Showing 25 to 36 of 114 entries