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DOI: 10.1055/a-2302-3294
Butadienyl Ketene: An Unexplored Intermediate in Organic Synthesis
Abstract
Butadienyl ketene is a useful intermediate because of its role as a 2p-component in cycloaddition reactions with a variety of substrates such as simple or conjugated imines and dienes. This review article summarizes recent reports on the generation of butadienyl ketene in situ and their cycloaddition reactions to afford heterocyclic systems. The chemistry of butadienyl ketene is explored with a focus on its [2+2] and [4+2] cycloaddition reactions with a variety of imines and azadiene derivatives such as 1,3-diazabuta-1,3-dienes, for the synthesis of four- and six-membered heterocycles, respectively.
Key words
ketenes - butadienyl ketene - dienyl ketene - [2+2] cycloaddition - [4+2] cycloaddition - lactams - pyrimidinonesPublication History
Received: 13 February 2024
Accepted after revision: 25 March 2024
Accepted Manuscript online:
09 April 2024
Article published online:
22 April 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1a Tidwell TT. Ketenes II . John Wiley & Sons; Hoboken: 2006
- 1b Temperley CM. In Comprehensive Organic Functional Group Transformations II, Vol. 3. Katritzky AR, Taylor RJ. K. Elsevier; Amsterdam: 2005: 573
- 1c Tidwell TT. Angew. Chem. Int. Ed. 2005; 44: 5778 ; Angew. Chem. 2005, 117, 5926
- 1d Danheiser RL. Three Carbon–Heteroatom Bonds: Ketenes and Derivatives: Science of Synthesis Original Edition, Vol. 23. Georg Thieme Verlag KG; Stuttgart: 2006
- 2a Tidwell TT. Eur. J. Org. Chem. 2006; 563
- 2b Louie J. Curr. Org. Chem. 2005; 9: 605
- 2c Tidwell TT. Angew. Chem. Int. Ed. 2005; 44: 6812 ; Angew. Chem. 2005, 117, 6973
- 2d Schaefer C, Fu GC. Angew. Chem. Int. Ed. 2005; 44: 4606 ; Angew. Chem. 2005, 117, 4682
- 2e Martin-Zamora E, Ferrete A, Llera JM, Munoz JM, Pappalardo RR, Fernandez R, Lassaletta JM. Chem. Eur. J. 2004; 10: 6111
- 2f Far AR. Angew. Chem. Int. Ed. 2003; 42: 2340 ; Angew. Chem. 2003, 115, 2442
- 3a Taing M, Moore HW. J. Org. Chem. 1996; 61: 329
- 3b Sun L, Liebeskind LS. J. Org. Chem. 1995; 60: 8194
- 3c Birchler AG, Liu F, Liebeskind LS. J. Org. Chem. 1994; 59: 7737
- 3d Gurski A, Liebeskind LS. J. Am. Chem. Soc. 1993; 115: 6101
- 3e Moore HW. Decker O. H. Chem. Rev. 1986; 86: 821
- 3f Moore HW, Yerxa BR. Chemtracts 1992; 5: 273
- 3g Hoye TR, Magee AS, Trumper WS. Synth. Commun. 1982; 12: 183
- 4 Sordo JA, Gonzalez J, Sordo TL. J. Am. Chem. Soc. 1992; 114: 6249
- 5 Bose AK, Banik BK, Manhas MS. Tetrahedron Lett. 1995; 36: 213 ; and references cited therein
- 6 The Organic Chemistry of (-Lactams . Georg GI. VCH; Weinheim: 1992. Chap. 6 and references cited therei
- 7 Manhas MS, Ghosh M, Bose AK. J. Org. Chem. 1990; 55: 575
- 8 Bose AK, Spiegelman G, Manhas MS. Tetrahedron Lett. 1971; 3167
- 9 Zamboni R, Just G. Can. J. Chem. 1979; 57: 1945
- 10a Bioorganic Chemistry: Peptides and Proteins . Hetch S. Oxford University Press; Oxford: 1998
- 10b Hesse M. Alkaloids: Nature’s Curse or Blessing?. Wiley-VCH; New York: 2000
- 11 Salzner U, Bachrach SM. J. Org. Chem. 1996; 61: 237
- 12a Tidwell TT. Top. Heterocycl. Chem. 2013; 30: 111
- 12b Mazumdar SN, Mahajan MP. Tetrahedron 1991; 47: 1473
- 12c Mazumdar SN, Ibnusaud I, Mahajan MP. Tetrahedron Lett. 1986; 27: 5875
- 12d Sharma AK, Mahajan MP. Tetrahedron 1997; 53: 13841
- 13 Sharma AK, Mazumdar SN, Mahajan MP. J. Org. Chem. 1995; 61: 5506
- 14a Sharma AK, Jayakumar S, Mahajan MP. Tetrahedron Lett. 1998; 39: 7205
- 14b Sharma AK, Kumar RS, Mahajan MP. Heterocycles 2000; 52: 603
- 15 Sharma AK, Jayakumar S, Hundal MS, Mahajan MP. J. Chem. Soc., Perkin Trans. 1 2002; 774
- 16a Bose AK, Spiegelman G, Manhas MS. Tetrahedron Lett. 1971; 3167
- 16b Bose AK, Krishanan L, Wagle DR, Manhas MS. Tetrahedron Lett. 1986; 27: 5955
- 16c Manhas MS, Ghosh M, Bose AK. J. Org. Chem. 1990; 55: 575
- 17 Kliegman JM, Barnes RK. J. Org. Chem. 1970; 35: 3140
- 18a Bains D, Kumar Y, Singh P, Bhargava G. J. Heterocycl. Chem. 2015; 53: 1665
- 18b Kumar Y, Singh P, Bhargava G. RSC Adv. 2016; 6: 99220
- 19 Kumar Y, Bedi PM, Singh P, Adeniyi AA, Singh-Pillay A, Singh P, Bhargava G. ChemistrySelect 2018; 3: 9484
- 20 Wang S, Malebari AM, Greene TF, Kandwal S, Fayne D, Nathwani SM, Zisterer DM, Twamley B, O’Boyle NM, Meegan MJ. Pharmaceuticals 2023; 16: 1000
- 21 Jayakumar S, Singh P, Mahajan MP. Tetrahedron 2004; 60: 4315