[2 + 2] Cycloaddition Reactions of Butadienyl Ketene with 1,4-Diazabuta-1,3-dienes: Synthesis of Functionalized Butadienyl-4-iminomethyl-azetidin-2-ones and Butenylidene-butadienyl-[2,2′-biazetidine]-4,4′-diones
Deepak Bains
Department of Applied Sciences, Punjab Technical University, Kapurthala, Punjab, 144603 India
Search for more papers by this authorYogesh Kumar
Department of Applied Sciences, Punjab Technical University, Kapurthala, Punjab, 144603 India
Search for more papers by this authorPrabhpreet Singh
Department of Chemistry, Guru Nanak Dev University, Amritsar, Punjab, 143005 India
Search for more papers by this authorCorresponding Author
Gaurav Bhargava
Department of Applied Sciences, Punjab Technical University, Kapurthala, Punjab, 144603 India
E-mail: [email protected]Search for more papers by this authorDeepak Bains
Department of Applied Sciences, Punjab Technical University, Kapurthala, Punjab, 144603 India
Search for more papers by this authorYogesh Kumar
Department of Applied Sciences, Punjab Technical University, Kapurthala, Punjab, 144603 India
Search for more papers by this authorPrabhpreet Singh
Department of Chemistry, Guru Nanak Dev University, Amritsar, Punjab, 143005 India
Search for more papers by this authorCorresponding Author
Gaurav Bhargava
Department of Applied Sciences, Punjab Technical University, Kapurthala, Punjab, 144603 India
E-mail: [email protected]Search for more papers by this authorAbstract
The reactions of butadienylketene with variety of 1,4-diazabuta-1,3-dienes are studied. The reactions resulted in the formation of previously unknown functionalized cis butadienyl-4-iminomethyl-azetidin-2-ones and butenylidene-butadienyl-[2,2′-biazetidine]-4,4′- diones. Butadienyl ketene reacts in [2+2] cycloaddition fashion with both iminic portion of 1,4- diazabuta-1,3-dienes and competitive [4+2] cycloaddition reaction of 1,4-diazabuta-1,3-dienes as 4π component with butadienyl ketene as 2π component are not observed.
Supporting Information
| Filename | Description |
|---|---|
| jhet2465-sup-0001-Supplementary.docxWord 2007 document , 152.6 KB | Supporting info item |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References and Notes
- 1(a) Bioorganic Chemistry: Peptides and Proteins; S. Hetch, Ed.; Oxford University Press: Oxford, 1998; (b) Hesse, M. Alkaloids: Nature's Curse or Blessing?; Wiley-VCH: New York, 2000.
- 2Salzner, U.; Bachrach, S. M. J Org Chem 1996, 61, 237.
- 3(a) Tidwell, T. T. Top Heterocycl Chem; Springer: Berlin Heidelberg, 2013; Vol 30, pp 111–145; (b)Mazumdar, S. N.; Mahajan, M. P. Tetrahedron 1991, 47, 1473; (c) Mazumdar, S. N.; Ibnusaud, I.; Mahajan, M. P. Tetrahedron Lett 1986, 27, 5875; (d) Sharma, A. K.; Mahajan, M. P. Tetrahedron 1997, 53, 13841.
- 4(a) Bose, A. K.; Spiegelman, G.; Manhas, M. S. Tetrahedron Lett 1971, 12, 3167;
10.1016/S0040-4039(01)97121-7 Google Scholar(b) Bose, A. K.; Krishanan, L.; Wagle, D. R.; Manhas, M. S. Tetrahedron Lett 1986, 27, 5955; (c) Manhas, M. S.; Ghosh, M.; Bose, A. K. J Org Chem 1990, 55, 575.
- 5(a) Mazumdar, S. N.; Mahajan, M. P. Synthesis 1990, 417; (b) Sharma, A. K.; Mazumdar, S. N.; Mahajan, M. P. J Org Chem 1996, 61, 5506.
- 6Singh, P.; Marwaha, A.; Singh, H.; Mahajan, M. P. Tetrahedron 2005, 61, 11999.
- 7(a) Sharma, A. K.; Jayakumar, S.; Hundal, M. S.; Mahajan, M. P. J Chem Soc Perkin Trans 1 2002, 774; (b) Sharma, A. K.; Jayakumar, S.; Mahajan, M. P. Tetrahedron Lett 1998, 39, 7205.
- 8Jayakumar, S.; Singh, P.; Mahajan, M. P. Tetrahedron 2004, 60, 4315.
- 9Bhargava, G.; Kumar, V.; Mahajan, M. P. Tetrahedron Lett 2007, 48, 2365.
- 10Singh, P.; Bhargava, G.; Kumar, V.; Mahajan, M. P. Tetrahedron Lett 2010, 51, 4272.
- 11Anand, A.; Bhargava, G.; Kumar, V.; Mahajan, M. P. Tetrahedron Lett 2010, 51, 2312.
- 12Mehra, V.; Kumar, V. Tetrahedron 2013, 69, 3857.
- 13Bhargava, G.; Mahajan, M. P.; Saito, T.; Otani, T.; Kurashima, M.; Sakai, K. Eur J Org Chem 2005, 2397.
- 14(a) Byler, K. G.; Arias, M. B.; Navarro, A. M.; Torres, B. N.; Bustillos, L. G. T.; Mayorga, K. M. Bioorg Med Chem 2012, 20, 2587; (b) Lorenc-Koci, E.; Smialowska, M.; Antkiewicz-Michaluk, L.; Golembiowska, K.; Bajkowska, M.; Wolfarth, S. Neuroscience 2000, 95, 1049.
- 15(a) Goel, R. K.; Kumar, V.; Mahajan, M. P. Bioorg Med Chem Lett 2005, 15, 2145; (b)Bedi, P. M. S.; Kumar, V.; Mahajan, M. P. Bioorg Med Chem Lett 2004, 14, 5211.
- 16(a) Mittal, M.; Goel, R. K.; Bhargava, G.; Mahajan, M. P. Bioorg Med Chem Lett 2008, 18, 5347; (b) Raj, R.; Mehra, V.; Singh, P.; Kumar, V.; Bhargava, G.; Mahajan, M. P.; Handa, S.; Slaughter, L. Eur J Org Chem 2011, 2697.
- 17Kumar, Y.; Kuila, B.; Mahajan, D.; Singh, P.; Mohapatra, B.; Bhargava, G. Tetrahedron Lett 2014, 55, 2793.
- 18Kumar, Y.; Singh, P.; Bhargava, G. Synlett 2015, 26, 363.
- 19(a) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Gomez-Campillos, G. Eur J Org Chem 2011, 364; (b) Wang, Z.; Chen, N.; Xu, J. Tetrahedron 2011, 67, 9690; (c) Alcaide, B.; Almendros, P. Chem Soc Rev 2001, 30, 226; (d) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem Rev 2007, 107, 4437.
- 20(a) Alcaide, B.; Almendros, P.; Cabrero, G.; Ruiz, M. P. Org Lett 2005, 7, 3981; (b) Alcaide, B.; Almendros, P.; Cabreroa, G.; Ruiza, M. P. Chem Commun 2007, 4788; (c) Krishnaswamy, D.; Govande, V. V.; Deshmukh, A. R. A. S. Synthesis 2003, 1903; (d) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Chem Eur J 2003, 9, 3415.
- 21(a) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Chem Commun 2000, 485; (b) Ojima, I.; Lin, S.; Inoue, T.; Miller, M. L.; Borella, C. P.; Geng, X.; Walsh, J. J. J Am Chem Soc 2000, 122, 5343.
- 22(a) Georg, G. I.; Kant, J.; Gill, H. S. J Am Chem Soc 1987, 109, 1129; (b) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett 1985, 26, 3783; (c) Fujisawa, T.; Shibuya, A.; Sato, D.; Shimizu, M. Synlett 1995, 1067; (d) Tsubouchi, H.; Tsuji, K.; Yusumura, K.; Tada, N.; Nishitani, S.; Minamikawa, J.; Ishikawa, H. Tetrahedron Asymmetry 1994, 5, 441.
- 23Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. J Chem Soc Perkin Trans 1 1999, 1083.
- 24Kliegman, J. M.; Barnes, R. K. J Org Chem 1970, 35, 3140.
