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Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion.

Organic & biomolecular chemistry

Sapegin A, Osipyan A, Krasavin M.
PMID: 28321443
Org Biomol Chem. 2017 Apr 05;15(14):2906-2909. doi: 10.1039/c7ob00535k.

Imidazoline-fused [1,4]oxazepines (prepared in two simple steps from methyl 2-hydroxyaroates, ethylene diamine and bis-electrophilic aromatics) undergo a facile, good-yielding hydrolytic imidazoline ring expansion (HIRE) upon N-alkylation and treatment with aqueous K

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Sapegin A, Osipyan A, Krasavin M. Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion. Org Biomol Chem. 2017;15(14):2906-2909doi: 10.1039/c7ob00535k.
Sapegin, A., Osipyan, A., & Krasavin, M. (2017). Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion. Organic & biomolecular chemistry, 15(14), 2906-2909. https://doi.org/10.1039/c7ob00535k
Sapegin, Alexander, et al. "Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion." Organic & biomolecular chemistry vol. 15,14 (2017): 2906-2909. doi: https://doi.org/10.1039/c7ob00535k
Sapegin A, Osipyan A, Krasavin M. Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion. Org Biomol Chem. 2017 Apr 05;15(14):2906-2909. doi: 10.1039/c7ob00535k. PMID: 28321443.
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Matrix-assisted laser desorption/ionization and electrospray ionization mass spectrometric study of 2,3-dihydro-1,4-benzoxazepines.

Rapid communications in mass spectrometry : RCM

Kéki S, Nagy L, Deák G, Lévai A, Zsuga M.
PMID: 15838925
Rapid Commun Mass Spectrom. 2005;19(10):1263-7. doi: 10.1002/rcm.1920.

Fragmentations of the protonated adduct ions [M+H](+) of seven 1,4-benzoxazepine derivatives were studied using 'post-source decay' matrix-assisted laser desorption/ionization (PSD MALDI) and electrospray nozzle-skimmer collisionally induced dissociation (ESI-CID) mass spectrometric methods. It was found that both methods generated mainly...

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Kéki S, Nagy L, Deák G, et al. Matrix-assisted laser desorption/ionization and electrospray ionization mass spectrometric study of 2,3-dihydro-1,4-benzoxazepines. Rapid Commun Mass Spectrom. 2005;19(10):1263-7doi: 10.1002/rcm.1920.
Kéki, S., Nagy, L., Deák, G., Lévai, A., & Zsuga, M. (2005). Matrix-assisted laser desorption/ionization and electrospray ionization mass spectrometric study of 2,3-dihydro-1,4-benzoxazepines. Rapid communications in mass spectrometry : RCM, 19(10), 1263-7. https://doi.org/10.1002/rcm.1920
Kéki, Sándor, et al. "Matrix-assisted laser desorption/ionization and electrospray ionization mass spectrometric study of 2,3-dihydro-1,4-benzoxazepines." Rapid communications in mass spectrometry : RCM vol. 19,10 (2005): 1263-7. doi: https://doi.org/10.1002/rcm.1920
Kéki S, Nagy L, Deák G, Lévai A, Zsuga M. Matrix-assisted laser desorption/ionization and electrospray ionization mass spectrometric study of 2,3-dihydro-1,4-benzoxazepines. Rapid Commun Mass Spectrom. 2005;19(10):1263-7. doi: 10.1002/rcm.1920. PMID: 15838925.
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Rh(II)/Mg(O.

Organic letters

Ko YO, Jeon HJ, Jung DJ, Kim UB, Lee SG.
PMID: 27978637
Org Lett. 2016 Dec 16;18(24):6432-6435. doi: 10.1021/acs.orglett.6b03328. Epub 2016 Dec 01.

A novel, one-pot route for the synthesis of nonaromatic ring-fused 1,4-oxazepines and 1,4-oxazines has been developed. The reaction features a sequential rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with glycidols, followed by a regioselective Lewis acid Mg(O

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Ko YO, Jeon HJ, Jung DJ, et al. Rh(II)/Mg(O. Org Lett. 2016;18(24):6432-6435doi: 10.1021/acs.orglett.6b03328.
Ko, Y. O., Jeon, H. J., Jung, D. J., Kim, U. B., & Lee, S. G. (2016). Rh(II)/Mg(O. Organic letters, 18(24), 6432-6435. https://doi.org/10.1021/acs.orglett.6b03328
Ko, Young Ok, et al. "Rh(II)/Mg(O." Organic letters vol. 18,24 (2016): 6432-6435. doi: https://doi.org/10.1021/acs.orglett.6b03328
Ko YO, Jeon HJ, Jung DJ, Kim UB, Lee SG. Rh(II)/Mg(O. Org Lett. 2016 Dec 16;18(24):6432-6435. doi: 10.1021/acs.orglett.6b03328. Epub 2016 Dec 01. PMID: 27978637.
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The Elusive Seven-Membered Cyclic Imino Ether Tetrahydrooxazepine.

Journal of the American Chemical Society

Verbraeken B, Hullaert J, van Guyse J, Van Hecke K, Winne J, Hoogenboom R.
PMID: 30508478
J Am Chem Soc. 2018 Dec 19;140(50):17404-17408. doi: 10.1021/jacs.8b10918. Epub 2018 Dec 10.

Cyclic imino ether heterocycles are used as ligands in transition metal catalysis, in various drugs and as reactive monomers in living cationic ring-opening polymerization (CROP). While five- and six-membered cyclic imino ethers, i.e. 2-oxazolines and 4,5-dihydro-1,3-oxazines, have extensively been...

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Verbraeken B, Hullaert J, van Guyse J, et al. The Elusive Seven-Membered Cyclic Imino Ether Tetrahydrooxazepine. J Am Chem Soc. 2018;140(50):17404-17408doi: 10.1021/jacs.8b10918.
Verbraeken, B., Hullaert, J., van Guyse, J., Van Hecke, K., Winne, J., & Hoogenboom, R. (2018). The Elusive Seven-Membered Cyclic Imino Ether Tetrahydrooxazepine. Journal of the American Chemical Society, 140(50), 17404-17408. https://doi.org/10.1021/jacs.8b10918
Verbraeken, Bart, et al. "The Elusive Seven-Membered Cyclic Imino Ether Tetrahydrooxazepine." Journal of the American Chemical Society vol. 140,50 (2018): 17404-17408. doi: https://doi.org/10.1021/jacs.8b10918
Verbraeken B, Hullaert J, van Guyse J, Van Hecke K, Winne J, Hoogenboom R. The Elusive Seven-Membered Cyclic Imino Ether Tetrahydrooxazepine. J Am Chem Soc. 2018 Dec 19;140(50):17404-17408. doi: 10.1021/jacs.8b10918. Epub 2018 Dec 10. PMID: 30508478.
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The base-promoted synthesis of multisubstituted benzo[b][1,4]oxazepines.

Chemical communications (Cambridge, England)

Shen J, Xue L, Lin X, Cheng G, Cui X.
PMID: 26776745
Chem Commun (Camb). 2016 Feb 25;52(16):3292-5. doi: 10.1039/c5cc09877g. Epub 2016 Jan 18.

A novel protocol to synthesize multisubstituted benzo[b][1,4]oxazepines from N-(2-haloaryl)enaminones has been developed. In this procedure, only 2 equiv. of Cs2CO3 was required. A variety of polysubstituted benzo[b][1,4]oxazepine derivatives were provided in up to 95% yield for 27 examples.

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Shen J, Xue L, Lin X, et al. The base-promoted synthesis of multisubstituted benzo[b][1,4]oxazepines. Chem Commun (Camb). 2016;52(16):3292-5doi: 10.1039/c5cc09877g.
Shen, J., Xue, L., Lin, X., Cheng, G., & Cui, X. (2016). The base-promoted synthesis of multisubstituted benzo[b][1,4]oxazepines. Chemical communications (Cambridge, England), 52(16), 3292-5. https://doi.org/10.1039/c5cc09877g
Shen, Jinhai, et al. "The base-promoted synthesis of multisubstituted benzo[b][1,4]oxazepines." Chemical communications (Cambridge, England) vol. 52,16 (2016): 3292-5. doi: https://doi.org/10.1039/c5cc09877g
Shen J, Xue L, Lin X, Cheng G, Cui X. The base-promoted synthesis of multisubstituted benzo[b][1,4]oxazepines. Chem Commun (Camb). 2016 Feb 25;52(16):3292-5. doi: 10.1039/c5cc09877g. Epub 2016 Jan 18. PMID: 26776745.
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Synthesis of substituted benzo[b][1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones.

Organic & biomolecular chemistry

Oshimoto K, Zhou B, Tsuji H, Kawatsura M.
PMID: 31894810
Org Biomol Chem. 2020 Jan 22;18(3):415-419. doi: 10.1039/c9ob02450f.

We have developed a novel synthetic method accessing benzo[b][1,4]oxazepines that are one of the rare classes of benzoxazepine derivatives by reaction of 2-aminophenols with alkynones in 1,4-dioxane at 100 °C. A series of benzo[b][1,4]oxazepine derivatives can be prepared by...

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Oshimoto K, Zhou B, Tsuji H, et al. Synthesis of substituted benzo[b][1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones. Org Biomol Chem. 2020;18(3):415-419doi: 10.1039/c9ob02450f.
Oshimoto, K., Zhou, B., Tsuji, H., & Kawatsura, M. (2020). Synthesis of substituted benzo[b][1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones. Organic & biomolecular chemistry, 18(3), 415-419. https://doi.org/10.1039/c9ob02450f
Oshimoto, Kohei, et al. "Synthesis of substituted benzo[b][1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones." Organic & biomolecular chemistry vol. 18,3 (2020): 415-419. doi: https://doi.org/10.1039/c9ob02450f
Oshimoto K, Zhou B, Tsuji H, Kawatsura M. Synthesis of substituted benzo[b][1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones. Org Biomol Chem. 2020 Jan 22;18(3):415-419. doi: 10.1039/c9ob02450f. PMID: 31894810.
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Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines.

Organic letters

Mollo MC, Orelli LR.
PMID: 27934376
Org Lett. 2016 Dec 02;18(23):6116-6119. doi: 10.1021/acs.orglett.6b03122. Epub 2016 Nov 22.

The first general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl

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Mollo MC, Orelli LR. Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines. Org Lett. 2016;18(23):6116-6119doi: 10.1021/acs.orglett.6b03122.
Mollo, M. C., & Orelli, L. R. (2016). Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines. Organic letters, 18(23), 6116-6119. https://doi.org/10.1021/acs.orglett.6b03122
Mollo, María C, and Orelli, Liliana R. "Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines." Organic letters vol. 18,23 (2016): 6116-6119. doi: https://doi.org/10.1021/acs.orglett.6b03122
Mollo MC, Orelli LR. Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines. Org Lett. 2016 Dec 02;18(23):6116-6119. doi: 10.1021/acs.orglett.6b03122. Epub 2016 Nov 22. PMID: 27934376.
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Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: access to oxygen-bridged tetrahydro-1,4-oxazepines.

Chemical communications (Cambridge, England)

Zhao Y, Wang C, Hu Y, Wan B.
PMID: 29577162
Chem Commun (Camb). 2018 Apr 17;54(32):3963-3966. doi: 10.1039/c8cc00881g.

A Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water is described. This process provides atom-economical access to oxygen-bridged tetrahydro-1,4-oxazepines, where the bridged oxygen atom originates from water. The unique property of the Brønsted acid shows distinct...

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Zhao Y, Wang C, Hu Y, et al. Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: access to oxygen-bridged tetrahydro-1,4-oxazepines. Chem Commun (Camb). 2018;54(32):3963-3966doi: 10.1039/c8cc00881g.
Zhao, Y., Wang, C., Hu, Y., & Wan, B. (2018). Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: access to oxygen-bridged tetrahydro-1,4-oxazepines. Chemical communications (Cambridge, England), 54(32), 3963-3966. https://doi.org/10.1039/c8cc00881g
Zhao, Yingying, et al. "Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: access to oxygen-bridged tetrahydro-1,4-oxazepines." Chemical communications (Cambridge, England) vol. 54,32 (2018): 3963-3966. doi: https://doi.org/10.1039/c8cc00881g
Zhao Y, Wang C, Hu Y, Wan B. Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: access to oxygen-bridged tetrahydro-1,4-oxazepines. Chem Commun (Camb). 2018 Apr 17;54(32):3963-3966. doi: 10.1039/c8cc00881g. PMID: 29577162.
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Ru-Catalyzed asymmetric transfer hydrogenation of substituted dibenzo[b,f][1,4]oxazepines in water.

Organic & biomolecular chemistry

More GV, Bhanage BM.
PMID: 28613337
Org Biomol Chem. 2017 Jun 27;15(25):5263-5267. doi: 10.1039/c7ob01229b.

This is the first report on the asymmetric transfer hydrogenation (ATH) of dibenzo[b,f][1,4]oxazepine compounds in the presence of an (R,R)-Ru-Ts-DPEN complex. The developed catalytic asymmetric protocol provides biologically active 11-substituted-10,11-dihydrodibenzo[b,f][1,4]oxazepines with excellent conversion (up to >99%) and high enantioselectivity...

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More GV, Bhanage BM. Ru-Catalyzed asymmetric transfer hydrogenation of substituted dibenzo[b,f][1,4]oxazepines in water. Org Biomol Chem. 2017;15(25):5263-5267doi: 10.1039/c7ob01229b.
More, G. V., & Bhanage, B. M. (2017). Ru-Catalyzed asymmetric transfer hydrogenation of substituted dibenzo[b,f][1,4]oxazepines in water. Organic & biomolecular chemistry, 15(25), 5263-5267. https://doi.org/10.1039/c7ob01229b
More, Ganesh V, and Bhanage, Bhalchandra M. "Ru-Catalyzed asymmetric transfer hydrogenation of substituted dibenzo[b,f][1,4]oxazepines in water." Organic & biomolecular chemistry vol. 15,25 (2017): 5263-5267. doi: https://doi.org/10.1039/c7ob01229b
More GV, Bhanage BM. Ru-Catalyzed asymmetric transfer hydrogenation of substituted dibenzo[b,f][1,4]oxazepines in water. Org Biomol Chem. 2017 Jun 27;15(25):5263-5267. doi: 10.1039/c7ob01229b. PMID: 28613337.
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Tetrahydro-1,3-oxazepines via Intramolecular Amination of Cyclopropylmethyl Cation.

Organic letters

Skvorcova M, Grigorjeva L, Jirgensons A.
PMID: 26039677
Org Lett. 2015 Jun 19;17(12):2902-4. doi: 10.1021/acs.orglett.5b01014. Epub 2015 Jun 03.

An efficient synthesis of tetrahydro-1,3-oxazepines was developed involving the regioselective intramolecular amination of cyclopropylmethyl cation. The cation was generated by the abstraction of one imidate group in bis-imidate bearing a carbocation-stabilizing substituent. Using 1,1,2,3-tetrasubstituted cyclopropane substrates, highly diastereoselective intramolecular...

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Skvorcova M, Grigorjeva L, Jirgensons A. Tetrahydro-1,3-oxazepines via Intramolecular Amination of Cyclopropylmethyl Cation. Org Lett. 2015;17(12):2902-4doi: 10.1021/acs.orglett.5b01014.
Skvorcova, M., Grigorjeva, L., & Jirgensons, A. (2015). Tetrahydro-1,3-oxazepines via Intramolecular Amination of Cyclopropylmethyl Cation. Organic letters, 17(12), 2902-4. https://doi.org/10.1021/acs.orglett.5b01014
Skvorcova, Marija, et al. "Tetrahydro-1,3-oxazepines via Intramolecular Amination of Cyclopropylmethyl Cation." Organic letters vol. 17,12 (2015): 2902-4. doi: https://doi.org/10.1021/acs.orglett.5b01014
Skvorcova M, Grigorjeva L, Jirgensons A. Tetrahydro-1,3-oxazepines via Intramolecular Amination of Cyclopropylmethyl Cation. Org Lett. 2015 Jun 19;17(12):2902-4. doi: 10.1021/acs.orglett.5b01014. Epub 2015 Jun 03. PMID: 26039677.
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Author Correction: Novel Indole-fused benzo-oxazepines (IFBOs) inhibit invasion of hepatocellular carcinoma by targeting IL-6 mediated JAK2/STAT3 oncogenic signals.

Scientific reports

Singh AK, Bhadauria AS, Kumar U, Raj V, Rai A, Kumar P, Keshari AK, Kumar D, Maity B, Nath S, Prakash A, Saha S.
PMID: 32024920
Sci Rep. 2020 Feb 06;10(1):2391. doi: 10.1038/s41598-020-59134-9.

An amendment to this paper has been published and can be accessed via a link at the top of the paper.

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Singh AK, Bhadauria AS, Kumar U, et al. Author Correction: Novel Indole-fused benzo-oxazepines (IFBOs) inhibit invasion of hepatocellular carcinoma by targeting IL-6 mediated JAK2/STAT3 oncogenic signals. Sci Rep. 2020;10(1):2391doi: 10.1038/s41598-020-59134-9.
Singh, A. K., Bhadauria, A. S., Kumar, U., Raj, V., Rai, A., Kumar, P., Keshari, A. K., Kumar, D., Maity, B., Nath, S., Prakash, A., & Saha, S. (2020). Author Correction: Novel Indole-fused benzo-oxazepines (IFBOs) inhibit invasion of hepatocellular carcinoma by targeting IL-6 mediated JAK2/STAT3 oncogenic signals. Scientific reports, 10(1), 2391. https://doi.org/10.1038/s41598-020-59134-9
Singh, Ashok K, et al. "Author Correction: Novel Indole-fused benzo-oxazepines (IFBOs) inhibit invasion of hepatocellular carcinoma by targeting IL-6 mediated JAK2/STAT3 oncogenic signals." Scientific reports vol. 10,1 (2020): 2391. doi: https://doi.org/10.1038/s41598-020-59134-9
Singh AK, Bhadauria AS, Kumar U, Raj V, Rai A, Kumar P, Keshari AK, Kumar D, Maity B, Nath S, Prakash A, Saha S. Author Correction: Novel Indole-fused benzo-oxazepines (IFBOs) inhibit invasion of hepatocellular carcinoma by targeting IL-6 mediated JAK2/STAT3 oncogenic signals. Sci Rep. 2020 Feb 06;10(1):2391. doi: 10.1038/s41598-020-59134-9. PMID: 32024920; PMCID: PMC7002741.
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Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement.

Organic & biomolecular chemistry

Hu F, Liu H, Jia J, Ma C.
PMID: 27845794
Org Biomol Chem. 2016 Nov 29;14(47):11076-11079. doi: 10.1039/c6ob02098d.

A one-pot transition-metal-free approach for the synthesis of indole-fused dibenzo[b,f][1,4]oxazepines from 2-(1H-indol-2-yl)phenol and 1,2-dihalobenzenes or 2 halonitroarenes has been developed. The proposed mechanism for this transformation features a Smiles rearrangement favoured over a direct intramolecular nucleophilic cyclization, which affords...

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Hu F, Liu H, Jia J, et al. Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement. Org Biomol Chem. 2016;14(47):11076-11079doi: 10.1039/c6ob02098d.
Hu, F., Liu, H., Jia, J., & Ma, C. (2016). Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement. Organic & biomolecular chemistry, 14(47), 11076-11079. https://doi.org/10.1039/c6ob02098d
Hu, Fangdong, et al. "Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement." Organic & biomolecular chemistry vol. 14,47 (2016): 11076-11079. doi: https://doi.org/10.1039/c6ob02098d
Hu F, Liu H, Jia J, Ma C. Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement. Org Biomol Chem. 2016 Nov 29;14(47):11076-11079. doi: 10.1039/c6ob02098d. PMID: 27845794.
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