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Formation of monocyclic and bicyclic aza-.beta.-lactams and other novel heterocycles from 1-(diphenylmethylene)-3-oxo-1,2-diazetidinium inner salt

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    Formation of monocyclic and bicyclic aza-.beta.-lactams and other novel heterocycles from 1-(diphenylmethylene)-3-oxo-1,2-diazetidinium inner salt
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    Cite this: J. Am. Chem. Soc. 1981, 103, 25, 7659–7660
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    https://doi.org/10.1021/ja00415a046
    Published December 1, 1981
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    This article is cited by 29 publications.

    1. Imre Gyűjtő, Márta Porcs-Makkay, Gergő Szabó, Zsolt Kelemen, Gyöngyvér Pusztai, Gábor Tóth, András Dancsó, Judit Halász, Gyula Simig, Balázs Volk, László Nyulászi. Basicity-Tuned Reactivity: diaza-[1,2]-Wittig versus diaza-[1,3]-Wittig Rearrangements of 3,4-Dihydro-2H-1,2,3-benzothiadiazine 1,1-Dioxides. The Journal of Organic Chemistry 2021, 86 (2) , 1685-1700. https://doi.org/10.1021/acs.joc.0c02512
    2. Wenjing Zhang, Yanyan Zhu, Donghui Wei, Yunxia Li, and Mingsheng Tang . Theoretical Investigations toward the [4 + 2] Cycloaddition of Ketenes with N-Benzoyldiazenes Catalyzed by N-Heterocyclic Carbenes: Mechanism and Enantioselectivity. The Journal of Organic Chemistry 2012, 77 (23) , 10729-10737. https://doi.org/10.1021/jo302044n
    3. Xue-Liang Huang, Xiang-Yu Chen and Song Ye. Enantioselective Synthesis of Aza-β-lactams via NHC-Catalyzed [2 + 2] Cycloaddition of Ketenes with Diazenedicarboxylates. The Journal of Organic Chemistry 2009, 74 (19) , 7585-7587. https://doi.org/10.1021/jo901656q
    4. Can Luo, Chun-Yan Guan, Zhen-Yu Li, Beiling Gao, Guang-Jian Mei. Dearomative spiroannulation of indoles enabled by the diaza-[1,2]-Wittig rearrangement. Organic Chemistry Frontiers 2024, 11 (6) , 1685-1691. https://doi.org/10.1039/D3QO02033A
    5. Frédéric Lecornué, Bastien Michelet. Four-Membered Rings With Two Nitrogen Atoms. 2022, 403-457. https://doi.org/10.1016/B978-0-12-818655-8.00153-0
    6. Auxiliadora Prieto. Synthesis of Four‐Membered Aza‐Heterocycles through Catalytic [2 + 2] Cycloaddition Reactions Assisted by Metal Complexes. 2020, 37-58. https://doi.org/10.1002/9781119708841.ch3
    7. Uroš Grošelj, Jurij Svete, . [3 + 2] Cycloadditions of Azomethine Imines. 2020, 529-930. https://doi.org/10.1002/0471264180.or103.02
    8. Marilia S. Santos, Andrew Nortcliffe, William Lewis, Tracey D. Bradshaw, Christopher J. Moody. Synthesis of Highly Substituted 1,2‐Diazetidin‐3‐ones, Small‐Ring Scaffolds for Drug Discovery. Chemistry – A European Journal 2018, 24 (33) , 8325-8330. https://doi.org/10.1002/chem.201801309
    9. Márta Porcs-Makkay, Imre Gyűjtő, Gyula Simig, Balázs Volk. Synthesis and base-mediated rearrangement of 3-acetyl-2-methyl-3,4-dihydro-2H-1,2,3-benzothiadiazine 1,1-dioxides. Tetrahedron 2016, 72 (51) , 8463-8469. https://doi.org/10.1016/j.tet.2016.11.021
    10. Louis N. Jungheim. The Chemistry of 1,2-Diazetidin-3-Ones. 2013, 145-174. https://doi.org/10.1016/B978-0-12-408100-0.00005-7
    11. Louis C. Morrill, Tomas Lebl, Alexandra M. Z. Slawin, Andrew D. Smith. Catalytic asymmetric α-amination of carboxylic acids using isothioureas. Chemical Science 2012, 3 (6) , 2088. https://doi.org/10.1039/c2sc20171b
    12. Donghui Wei, Yanyan Zhu, Cong Zhang, Dongzhen Sun, Wenjing Zhang, Mingsheng Tang. A DFT study on enantioselective synthesis of aza-β-lactams via NHC-catalyzed [2+2] cycloaddition of ketenes with diazenedicarboxylates. Journal of Molecular Catalysis A: Chemical 2011, 334 (1-2) , 108-115. https://doi.org/10.1016/j.molcata.2010.11.004
    13. Timothy R. Blackmore, Philip E. Thompson. Imidazolidin-4-ones: Their Syntheses and Applications. HETEROCYCLES 2011, 83 (9) , 1953. https://doi.org/10.3987/REV-11-707
    14. Xue‐Liang Huang, Lin He, Pan‐Lin Shao, Song Ye. [4+2] Cycloaddition of Ketenes with N ‐Benzoyldiazenes Catalyzed by N‐Heterocyclic Carbenes. Angewandte Chemie 2009, 121 (1) , 198-201. https://doi.org/10.1002/ange.200804487
    15. Xue‐Liang Huang, Lin He, Pan‐Lin Shao, Song Ye. [4+2] Cycloaddition of Ketenes with N ‐Benzoyldiazenes Catalyzed by N‐Heterocyclic Carbenes. Angewandte Chemie International Edition 2009, 48 (1) , 192-195. https://doi.org/10.1002/anie.200804487
    16. Ali Elriati, Jutta Loose, Roswitha Mayrhofer, Hans-Joachim Bergmann, Hans-Hartwig Otto. β-Lactam derivatives as enzyme inhibitors: halogenated β-lactams and related compounds. Monatshefte für Chemie - Chemical Monthly 2008, 139 (7) , 835-846. https://doi.org/10.1007/s00706-007-0837-5
    17. B.B. Lohray, V.B. Lohray, B.K. Srivastava. Four-membered Rings with Two Nitrogen Atoms. 2008, 623-687. https://doi.org/10.1016/B978-008044992-0.00213-3
    18. Yong Gong, Mark J Bausch, Linhua Wang. Acylimine mediated N N bond cleavage of pyrazolidinediones and subsequent conversion to dihydropyrimidinediones and malonamides. Tetrahedron Letters 2001, 42 (1) , 1-4. https://doi.org/10.1016/S0040-4039(00)01865-7
    19. Braj B. Lohray, Vidya Bhushan. Four-membered Rings with Two Nitrogen Atoms. 1996, 911-968. https://doi.org/10.1016/B978-008096518-5.00030-7
    20. Stanislav Rádl. Bicyclic Systems with Two Ring Junction Nitrogen Atoms. 1996, 747-832. https://doi.org/10.1016/B978-008096518-5.00198-2
    21. . Volume 1 References. 1996, 1215-1369. https://doi.org/10.1016/B978-008096518-5.00247-1
    22. . Volume 8 References. 1996, 1169-1326. https://doi.org/10.1016/B978-008096518-5.00254-9
    23. Dietrich Moderhack. Oxo‐ and imino‐functionalized 1,2‐oxazetidines. An overview. Journal of Heterocyclic Chemistry 1993, 30 (3) , 579-591. https://doi.org/10.1002/jhet.5570300301
    24. Edward C. Taylor, Denis M. Sobieray. “Bicyclobenzodiazepinones” from 3-oxo-1,2-diazetidinium hydroxide, inner salts. Tetrahedron 1991, 47 (46) , 9599-9620. https://doi.org/10.1016/S0040-4020(01)91027-0
    25. Helmut Quast, Georg Meichsner, Dieter Regnat, Klaus Banert, Eva‐Maria Peters, Karl Peters, Hans Georg von Schnering. Ein 1,5‐Diazabicyclo[3.3.0]octa‐2,7‐dien aus Acetylendicarbonsäure‐dimethylester und einem 3,5‐Dihydro‐4 H ‐1,2,3‐triazol‐4‐on. Liebigs Annalen der Chemie 1990, 1990 (5) , 465-467. https://doi.org/10.1002/jlac.199019900188
    26. Jacqueline Marchand-Brynaert, Léon Ghosez. Non β-Lactam Analogs of Penicillins and Cephalosporins. 1990, 727-794. https://doi.org/10.1007/978-3-642-75617-7_20
    27. Christopher J. Moody, Christopher J. Pearson, Geoffrey Lawton. Synthesis of aza-β-lactams by rhodium carbenoid mediated cyclisation. Tetrahedron Letters 1985, 26 (26) , 3171-3172. https://doi.org/10.1016/S0040-4039(00)98648-9
    28. A.K. Forrest, Richard R. Schmidt. De novo-synthesis of carbohydrates preparation of 4-amino-4-deoxy-d,l-ribose derivatives. Tetrahedron Letters 1984, 25 (17) , 1769-1772. https://doi.org/10.1016/S0040-4039(01)90037-1
    29. E. C. TAYLOR, R. J. CLEMENS, H. M. L. DAVIES, N. F. HALEY. ChemInform Abstract: FORMATION OF MONOCYCLIC AND BICYCLIC AZA‐β‐LACTAMS AND OTHER NOVEL HETEROCYCLES FROM 1‐(DIPHENYLMETHYLENE)‐3‐OXO‐1,2‐DIAZETIDINIUM INNER SALT. Chemischer Informationsdienst 1982, 13 (13) https://doi.org/10.1002/chin.198213113
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 1981, 103, 25, 7659–7660
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja00415a046
    Published December 1, 1981
    Request reuse permissions

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