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Correction: Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones.

Organic & biomolecular chemistry

Mtiraoui H, Renault K, Sanselme M, Msaddek M, Renard PY, Sabot C.
PMID: 28840214
Org Biomol Chem. 2017 Sep 13;15(35):7474-7475. doi: 10.1039/c7ob90126g.

Correction for 'Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones' by Hasan Mtiraoui, et al., Org. Biomol. Chem., 2017, 15, 3060-3068.

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Mtiraoui H, Renault K, Sanselme M, et al. Correction: Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones. Org Biomol Chem. 2017;15(35):7474-7475doi: 10.1039/c7ob90126g.
Mtiraoui, H., Renault, K., Sanselme, M., Msaddek, M., Renard, P. Y., & Sabot, C. (2017). Correction: Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones. Organic & biomolecular chemistry, 15(35), 7474-7475. https://doi.org/10.1039/c7ob90126g
Mtiraoui, Hasan, et al. "Correction: Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones." Organic & biomolecular chemistry vol. 15,35 (2017): 7474-7475. doi: https://doi.org/10.1039/c7ob90126g
Mtiraoui H, Renault K, Sanselme M, Msaddek M, Renard PY, Sabot C. Correction: Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones. Org Biomol Chem. 2017 Sep 13;15(35):7474-7475. doi: 10.1039/c7ob90126g. PMID: 28840214.
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Synthesis and biological evaluation of novel 1,4-benzodiazepin-3-one derivatives as potential antitumor agents against prostate cancer.

Bioorganic & medicinal chemistry

Vézina-Dawod S, Perreault M, Guay LD, Gerber N, Gobeil S, Biron E.
PMID: 34333393
Bioorg Med Chem. 2021 Sep 01;45:116314. doi: 10.1016/j.bmc.2021.116314. Epub 2021 Jul 21.

A novel tumor suppressing agent was discovered against PC-3 prostate cancer cells from the screening of a 1,4-benzodiazepin-3-one library. In this study, 96 highly diversified 2,4,5-trisubstituted 1,4-benzodiazepin-3-one derivatives were prepared by a two-step approach using sequential Ugi multicomponent reaction...

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Vézina-Dawod S, Perreault M, Guay LD, et al. Synthesis and biological evaluation of novel 1,4-benzodiazepin-3-one derivatives as potential antitumor agents against prostate cancer. Bioorg Med Chem. 2021;45:116314doi: 10.1016/j.bmc.2021.116314.
Vézina-Dawod, S., Perreault, M., Guay, L. D., Gerber, N., Gobeil, S., & Biron, E. (2021). Synthesis and biological evaluation of novel 1,4-benzodiazepin-3-one derivatives as potential antitumor agents against prostate cancer. Bioorganic & medicinal chemistry, 45116314. https://doi.org/10.1016/j.bmc.2021.116314
Vézina-Dawod, Simon, et al. "Synthesis and biological evaluation of novel 1,4-benzodiazepin-3-one derivatives as potential antitumor agents against prostate cancer." Bioorganic & medicinal chemistry vol. 45 (2021): 116314. doi: https://doi.org/10.1016/j.bmc.2021.116314
Vézina-Dawod S, Perreault M, Guay LD, Gerber N, Gobeil S, Biron E. Synthesis and biological evaluation of novel 1,4-benzodiazepin-3-one derivatives as potential antitumor agents against prostate cancer. Bioorg Med Chem. 2021 Sep 01;45:116314. doi: 10.1016/j.bmc.2021.116314. Epub 2021 Jul 21. PMID: 34333393.
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A Combination of Flow and Batch Mode Processes for the Efficient Preparation of mGlu.

Tetrahedron

Dhanya RP, Herath A, Sheffler DJ, Cosford NDP.
PMID: 30705468
Tetrahedron. 2018 Jun 21;74(25):3165-3170. doi: 10.1016/j.tet.2018.03.068. Epub 2018 Mar 30.

Benzodiazepinones are privileged scaffolds with activity against multiple therapeutically relevant biological targets. In support of our ongoing studies around allosteric modulators of metabotropic glutamate receptors (mGlus) we required the multigram synthesis of a β-ketoester key intermediate. We report the...

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Dhanya RP, Herath A, Sheffler DJ, et al. A Combination of Flow and Batch Mode Processes for the Efficient Preparation of mGlu. Tetrahedron. 2018;74(25):3165-3170doi: 10.1016/j.tet.2018.03.068.
Dhanya, R. P., Herath, A., Sheffler, D. J., & Cosford, N. D. P. (2018). A Combination of Flow and Batch Mode Processes for the Efficient Preparation of mGlu. Tetrahedron, 74(25), 3165-3170. https://doi.org/10.1016/j.tet.2018.03.068
Dhanya, Raveendra Panickar, et al. "A Combination of Flow and Batch Mode Processes for the Efficient Preparation of mGlu." Tetrahedron vol. 74,25 (2018): 3165-3170. doi: https://doi.org/10.1016/j.tet.2018.03.068
Dhanya RP, Herath A, Sheffler DJ, Cosford NDP. A Combination of Flow and Batch Mode Processes for the Efficient Preparation of mGlu. Tetrahedron. 2018 Jun 21;74(25):3165-3170. doi: 10.1016/j.tet.2018.03.068. Epub 2018 Mar 30. PMID: 30705468; PMCID: PMC6349389.
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Synthesis of Tetrazolo-Fused Benzodiazepines and Benzodiazepinones by a Two-Step Protocol Using an Ugi-Azide Reaction for Initial Diversity Generation.

Tetrahedron

Gunawan S, Ayaz M, De Moliner F, Frett B, Kaiser C, Patrick N, Xu Z, Hulme C.
PMID: 22923851
Tetrahedron. 2012 Jul 08;68(27):5606-5611. doi: 10.1016/j.tet.2012.04.068. Epub 2012 Apr 26.

A two-step strategy for the synthesis of arrays of tricyclic tetrazolo-fused benzodiazepines and benzodiazepinones has been investigated. The protocol uses ortho-N-Boc phenylisocyanides and phenylglyoxaldehydes or ethyl glyoxylate in the 4-component Ugi-Azide reaction to afford MCR (Multi Component Reactions) derived...

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Gunawan S, Ayaz M, De Moliner F, et al. Synthesis of Tetrazolo-Fused Benzodiazepines and Benzodiazepinones by a Two-Step Protocol Using an Ugi-Azide Reaction for Initial Diversity Generation. Tetrahedron. 2012;68(27):5606-5611doi: 10.1016/j.tet.2012.04.068.
Gunawan, S., Ayaz, M., De Moliner, F., Frett, B., Kaiser, C., Patrick, N., Xu, Z., & Hulme, C. (2012). Synthesis of Tetrazolo-Fused Benzodiazepines and Benzodiazepinones by a Two-Step Protocol Using an Ugi-Azide Reaction for Initial Diversity Generation. Tetrahedron, 68(27), 5606-5611. https://doi.org/10.1016/j.tet.2012.04.068
Gunawan, Steven, et al. "Synthesis of Tetrazolo-Fused Benzodiazepines and Benzodiazepinones by a Two-Step Protocol Using an Ugi-Azide Reaction for Initial Diversity Generation." Tetrahedron vol. 68,27 (2012): 5606-5611. doi: https://doi.org/10.1016/j.tet.2012.04.068
Gunawan S, Ayaz M, De Moliner F, Frett B, Kaiser C, Patrick N, Xu Z, Hulme C. Synthesis of Tetrazolo-Fused Benzodiazepines and Benzodiazepinones by a Two-Step Protocol Using an Ugi-Azide Reaction for Initial Diversity Generation. Tetrahedron. 2012 Jul 08;68(27):5606-5611. doi: 10.1016/j.tet.2012.04.068. Epub 2012 Apr 26. PMID: 22923851; PMCID: PMC3423981.
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Evaluation of two pairs of chiral stationary phases: effects from the length of the achiral spacers.

Chirality

Thunberg L, Allenmark S, Friberg A, Ek F, Frejd T.
PMID: 15390085
Chirality. 2004 Nov;16(9):614-24. doi: 10.1002/chir.20080.

Two pairs of chiral stationary phases (CSPs) with different C(2)-symmetric central parts were prepared and evaluated by chromatography of a series of structurally different racemates. Within each pair, the selectors on which the CSPs are based had different lengths...

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Thunberg L, Allenmark S, Friberg A, et al. Evaluation of two pairs of chiral stationary phases: effects from the length of the achiral spacers. Chirality. 2004;16(9):614-24doi: 10.1002/chir.20080.
Thunberg, L., Allenmark, S., Friberg, A., Ek, F., & Frejd, T. (2004). Evaluation of two pairs of chiral stationary phases: effects from the length of the achiral spacers. Chirality, 16(9), 614-24. https://doi.org/10.1002/chir.20080
Thunberg, Linda, et al. "Evaluation of two pairs of chiral stationary phases: effects from the length of the achiral spacers." Chirality vol. 16,9 (2004): 614-24. doi: https://doi.org/10.1002/chir.20080
Thunberg L, Allenmark S, Friberg A, Ek F, Frejd T. Evaluation of two pairs of chiral stationary phases: effects from the length of the achiral spacers. Chirality. 2004 Nov;16(9):614-24. doi: 10.1002/chir.20080. PMID: 15390085.
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Regioselective Halogenation of 1,4-Benzodiazepinones via CH Activation.

Scientific reports

Abdelkafi H, Cintrat JC.
PMID: 26179245
Sci Rep. 2015 Jul 16;5:12131. doi: 10.1038/srep12131.

This article reports an efficient CH activation process for regioselective halogenation of 1,4-benzodiazepinones. Direct halogenation with NXS (X = Br, I) affords halogenated benzodiazepinones on the central aromatic ring whereas catalyst (Pd(OAc)2) controlled CH activation furnishes regioselectively ortho halogenated...

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Abdelkafi H, Cintrat JC. Regioselective Halogenation of 1,4-Benzodiazepinones via CH Activation. Sci Rep. 2015;5:12131doi: 10.1038/srep12131.
Abdelkafi, H., & Cintrat, J. C. (2015). Regioselective Halogenation of 1,4-Benzodiazepinones via CH Activation. Scientific reports, 512131. https://doi.org/10.1038/srep12131
Abdelkafi, Hajer, and Cintrat, Jean-Christophe. "Regioselective Halogenation of 1,4-Benzodiazepinones via CH Activation." Scientific reports vol. 5 (2015): 12131. doi: https://doi.org/10.1038/srep12131
Abdelkafi H, Cintrat JC. Regioselective Halogenation of 1,4-Benzodiazepinones via CH Activation. Sci Rep. 2015 Jul 16;5:12131. doi: 10.1038/srep12131. PMID: 26179245; PMCID: PMC4503988.
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Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination.

Tetrahedron letters

Karyakarte SD, Sequeira FC, Zibreg GH, Huang G, Matthew JP, Ferreira MM, Chemler SR.
PMID: 26034340
Tetrahedron Lett. 2015 Jun 03;56(23):3686-3689. doi: 10.1016/j.tetlet.2015.01.171.

A new method for the synthesis of 2-aminomethyl functionalized 1,4-benzodiazepin-5-ones is presented. The benzodiazepine core is well-known to interact with biological receptors and many pharmaceutical drugs are derived from this structure. The alkene diamination strategy is employed for the...

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Karyakarte SD, Sequeira FC, Zibreg GH, et al. Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination. Tetrahedron Lett. 2015;56(23):3686-3689doi: 10.1016/j.tetlet.2015.01.171.
Karyakarte, S. D., Sequeira, F. C., Zibreg, G. H., Huang, G., Matthew, J. P., Ferreira, M. M., & Chemler, S. R. (2015). Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination. Tetrahedron letters, 56(23), 3686-3689. https://doi.org/10.1016/j.tetlet.2015.01.171
Karyakarte, Shuklendu D, et al. "Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination." Tetrahedron letters vol. 56,23 (2015): 3686-3689. doi: https://doi.org/10.1016/j.tetlet.2015.01.171
Karyakarte SD, Sequeira FC, Zibreg GH, Huang G, Matthew JP, Ferreira MM, Chemler SR. Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination. Tetrahedron Lett. 2015 Jun 03;56(23):3686-3689. doi: 10.1016/j.tetlet.2015.01.171. PMID: 26034340; PMCID: PMC4448762.
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Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring.

Beilstein journal of organic chemistry

Pérez-Torralba M, Claramunt RM, Angeles García M, López C, Torralba MC, Rosario Torres M, Alkorta I, Elguero J.
PMID: 24204428
Beilstein J Org Chem. 2013 Oct 21;9:2156-67. doi: 10.3762/bjoc.9.253. eCollection 2013.

Two novel tetrafluorinated 1,5-benzodiazepinones were synthesized and their X-ray structures determined. 6,7,8,9-Tetrafluoro-4-methyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one crystallizes in the monoclinic P21/c space group and 6,7,8,9-tetrafluoro-1,4-dimethyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one in the triclinic P-1 space group. Density functional theory studies at the B3LYP/6-311++G(d,p) level were carried out on...

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Pérez-Torralba M, Claramunt RM, Angeles García M, et al. Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring. Beilstein J Org Chem. 2013;9:2156-67doi: 10.3762/bjoc.9.253.
Pérez-Torralba, M., Claramunt, R. M., Angeles García, M., López, C., Torralba, M. C., Rosario Torres, M., Alkorta, I., & Elguero, J. (2013). Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring. Beilstein journal of organic chemistry, 92156-67. https://doi.org/10.3762/bjoc.9.253
Pérez-Torralba, Marta, et al. "Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring." Beilstein journal of organic chemistry vol. 9 (2013): 2156-67. doi: https://doi.org/10.3762/bjoc.9.253
Pérez-Torralba M, Claramunt RM, Angeles García M, López C, Torralba MC, Rosario Torres M, Alkorta I, Elguero J. Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring. Beilstein J Org Chem. 2013 Oct 21;9:2156-67. doi: 10.3762/bjoc.9.253. eCollection 2013. PMID: 24204428; PMCID: PMC3817505.
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Advances in [4+3]-Annulation/Cycloaddition Reactions Leading to Homo- and Heterocycles with Seven-Membered Rings.

Chemistry, an Asian journal

Selvaraj K, Chauhan S, Sandeep K, Swamy KCK.
PMID: 32519407
Chem Asian J. 2020 Aug 17;15(16):2380-2402. doi: 10.1002/asia.202000545. Epub 2020 Jul 02.

In this review, we summarize advances in [4+3] and a few other annulation/cycloaddition reactions for the construction of seven membered rings, with an emphasis on the literature subsequent to the year 2010. The type of products include the following:...

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Selvaraj K, Chauhan S, Sandeep K, et al. Advances in [4+3]-Annulation/Cycloaddition Reactions Leading to Homo- and Heterocycles with Seven-Membered Rings. Chem Asian J. 2020;15(16):2380-2402doi: 10.1002/asia.202000545.
Selvaraj, K., Chauhan, S., Sandeep, K., & Swamy, K. C. K. (2020). Advances in [4+3]-Annulation/Cycloaddition Reactions Leading to Homo- and Heterocycles with Seven-Membered Rings. Chemistry, an Asian journal, 15(16), 2380-2402. https://doi.org/10.1002/asia.202000545
Selvaraj, Karuppu, et al. "Advances in [4+3]-Annulation/Cycloaddition Reactions Leading to Homo- and Heterocycles with Seven-Membered Rings." Chemistry, an Asian journal vol. 15,16 (2020): 2380-2402. doi: https://doi.org/10.1002/asia.202000545
Selvaraj K, Chauhan S, Sandeep K, Swamy KCK. Advances in [4+3]-Annulation/Cycloaddition Reactions Leading to Homo- and Heterocycles with Seven-Membered Rings. Chem Asian J. 2020 Aug 17;15(16):2380-2402. doi: 10.1002/asia.202000545. Epub 2020 Jul 02. PMID: 32519407.
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Evaluation of a chiral stationary phase derived from a simple Diels-Alder reaction.

Chirality

Thunberg L, Allenmark S.
PMID: 12692885
Chirality. 2003 May 15;15(5):400-8. doi: 10.1002/chir.10224.

The bicyclic, C(2)-symmetric dicarboxylic acid obtained from the cycloaddition of fumaric acid to anthracene can readily be prepared in enantiomerically pure form on a large scale. Conversion of either enantiomer of the diacid into its corresponding bis-allylamide yields a...

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Thunberg L, Allenmark S. Evaluation of a chiral stationary phase derived from a simple Diels-Alder reaction. Chirality. 2003;15(5):400-8doi: 10.1002/chir.10224.
Thunberg, L., & Allenmark, S. (2003). Evaluation of a chiral stationary phase derived from a simple Diels-Alder reaction. Chirality, 15(5), 400-8. https://doi.org/10.1002/chir.10224
Thunberg, Linda, and Allenmark, Stig. "Evaluation of a chiral stationary phase derived from a simple Diels-Alder reaction." Chirality vol. 15,5 (2003): 400-8. doi: https://doi.org/10.1002/chir.10224
Thunberg L, Allenmark S. Evaluation of a chiral stationary phase derived from a simple Diels-Alder reaction. Chirality. 2003 May 15;15(5):400-8. doi: 10.1002/chir.10224. PMID: 12692885.
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Benzodiazepinone Derivatives as CRTH2 Antagonists.

ACS medicinal chemistry letters

Liu JJ, Cheng AC, Tang HL, Medina JC.
PMID: 24900341
ACS Med Chem Lett. 2011 Apr 17;2(7):515-8. doi: 10.1021/ml200019y. eCollection 2011 Jul 14.

Multiple CRTH2 antagonists are currently evaluated in human clinical trials for asthma and chronic obstructive pulmonary disease (COPD). During our lead optimization for CRTH2 antagonists, an observation of an intramolecular hydrogen bond in ortho-phenylsulfonamido benzophenone derivatives led to the...

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Liu JJ, Cheng AC, Tang HL, et al. Benzodiazepinone Derivatives as CRTH2 Antagonists. ACS Med Chem Lett. 2011;2(7):515-8doi: 10.1021/ml200019y.
Liu, J. J., Cheng, A. C., Tang, H. L., & Medina, J. C. (2011). Benzodiazepinone Derivatives as CRTH2 Antagonists. ACS medicinal chemistry letters, 2(7), 515-8. https://doi.org/10.1021/ml200019y
Liu, Jiwen Jim, et al. "Benzodiazepinone Derivatives as CRTH2 Antagonists." ACS medicinal chemistry letters vol. 2,7 (2011): 515-8. doi: https://doi.org/10.1021/ml200019y
Liu JJ, Cheng AC, Tang HL, Medina JC. Benzodiazepinone Derivatives as CRTH2 Antagonists. ACS Med Chem Lett. 2011 Apr 17;2(7):515-8. doi: 10.1021/ml200019y. eCollection 2011 Jul 14. PMID: 24900341; PMCID: PMC4018144.
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