A Simple and Direct Synthesis of 3-Methylene-1, 4-diarylazetidin-2-ones and (E)-3-Arylidene-1-phenylazetidin-2-ones Using Baylis–Hillman Derivatives
Manickam Bakthadoss A B C , Jayakumar Srinivasan B and Raman Selvakumar B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, Pondicherry University, Puducherry 605 014, India.
B Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
C Corresponding author. Email: bhakthadoss@yahoo.com
Australian Journal of Chemistry 67(2) 295-301 https://doi.org/10.1071/CH13382
Submitted: 30 July 2013 Accepted: 14 October 2013 Published: 2 December 2013
Abstract
Herein we describe a direct method, promoted by potassium tert-butoxide (KOtBu), for the synthesis of highly substituted α-methylene β-lactams and α-arylidene β-lactams from the amino ester intermediates derived from the acetates and bromo derivatives of the Baylis–Hillman adducts. A variety of β-lactams was synthesized in a single step with good yields.
References
[1] (a) For selected reviews, see: B. K. Hubbard, C. T. Walsh, Angew. Chem. Int. Ed. 2003, 42, 730.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhvFWmt7o%3D&md5=100fc007002802de25d234a0454f7247CAS |
(b) R. Nau, A. Eiffert, Clin. Microbiol. Rev. 2002, 15, 95.
| Crossref | GoogleScholarGoogle Scholar |
(c) G. Veinberg, M. Vorona, I. Shestakova, I. Kanepe, E. Lukevics, Curr. Med. Chem. 2003, 10, 1741.
| Crossref | GoogleScholarGoogle Scholar |
(d) E. L. Setti, R. G. Micetich, Curr. Med. Chem. 1998, 5, 101.
(e) G. I. Georg, Ed., The Organic Chemistry of β-Lactams 1993 (VCH: New York).
(f) G. S. Singh, Mini-Rev. Med. Chem. 2004, 4, 69.
| Crossref | GoogleScholarGoogle Scholar |
[2] (a) B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Rev. 2007, 107, 4437.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXotFeitrs%3D&md5=d537edcd33dadb080b6d7c0918d27218CAS | 17649981PubMed |
(b) I. Ojima, Acc. Chem. Res. 1995, 28, 383.
| Crossref | GoogleScholarGoogle Scholar |
(c) M. Suffness, Ed., Taxol Science and Applications 1995, pp. 3–25 (CRC Press, Boca Raton, FL).
(d) B. Alcaide, P. Almendros, Curr. Med. Chem. 2004, 11, 1921.
| Crossref | GoogleScholarGoogle Scholar |
(e) I. Ojima, F. Delaloge, Chem. Soc. Rev. 1997, 26, 377.
| Crossref | GoogleScholarGoogle Scholar |
[3] (a) D. Basavaiah, B. S. Reddy, S. S. Badsara, Chem. Rev. 2010, 110, 5447.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtVKmtbbM&md5=49989754ac3e337fb3a9c67ef45ba5feCAS | 20735052PubMed |
(b) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811.
| Crossref | GoogleScholarGoogle Scholar |
(c) V. Declerck, J. Martinez, F. Lamaty, Chem. Rev. 2009, 109, 1.
| Crossref | GoogleScholarGoogle Scholar |
(d) D. Basavaiah, K. V. Rao, R. J. Reddy, Chem. Soc. Rev. 2007, 36, 1581.
| Crossref | GoogleScholarGoogle Scholar |
(e) V. Singh, S. Batra, Tetrahedron 2008, 64, 4511.
| Crossref | GoogleScholarGoogle Scholar |
(f) D. Basavaiah, P. D. Rao, S. R. Hyma, Tetrahedron 1996, 52, 8001.
| Crossref | GoogleScholarGoogle Scholar |
[4] (a) D. Basavaiah, J. S. Rao, R. J. Reddy, J. Org. Chem. 2004, 69, 7379.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXnsVOqur0%3D&md5=d65cbef0a41dca247f38d0bbffff5c00CAS | 15471499PubMed |
(b) B. M. Trost, O. R. Thiel, H.-C. Tsui, J. Am. Chem. Soc. 2002, 124, 11616.
| Crossref | GoogleScholarGoogle Scholar |
(c) M. Saquib, M. K. Gupta, R. Sagar, Y. S. Prabhakar, A. K. Shaw, R. Kumar, P. R. Maulik, A. N. Gaikwad, S. Sinha, A. K. Srivastava, V. Chaturvedi, R. Srivastava, B. S. Srivastava, J. Med. Chem. 2007, 50, 2942.
| Crossref | GoogleScholarGoogle Scholar |
(d) V. Singh, R. Saxena, S. Batra, J. Org. Chem. 2005, 70, 353.
| Crossref | GoogleScholarGoogle Scholar |
(e) S. Batra, A. K. Roy, A. Patra, A. P. Bhaduri, W. R. Surin, S. A. V. Raghavan, P. Sharma, K. Kapoorb, M. Dikshit, Bioorg. Med. Chem. 2004, 12, 2059.
| Crossref | GoogleScholarGoogle Scholar |
(f) G. W. Amarante, F. Coelho, Tetrahedron 2010, 66, 6749.
| Crossref | GoogleScholarGoogle Scholar |
(g) Y. Zulykama, P. T. Perumal, Tetrahedron Lett. 2009, 50, 3892.
| Crossref | GoogleScholarGoogle Scholar |
(h) D. Basavaiah, M. Krishnamacharyula, R. S. Hyma, P. K. S. Sarma, N. Kumaragurubaran, J. Org. Chem. 1999, 64, 1197.
| Crossref | GoogleScholarGoogle Scholar |
(i) Y.-Q. Jiang, Y.-L. Shi, M. Shi, J. Am. Chem. Soc 2008, 130, 7202.
| Crossref | GoogleScholarGoogle Scholar |
(j) P. Auvray, P. Knochel, J. F. Normant, Tetrahedron Lett. 1986, 27, 5095.
| Crossref | GoogleScholarGoogle Scholar |
(k) A. Weichert, H. M. R. Hoffmann, J. Org. Chem. 1991, 56, 4098.
| Crossref | GoogleScholarGoogle Scholar |
[5] (a) M. Bakthadoss, G. Sivakumar, D. Kannan, Org. Lett. 2009, 11, 4466.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVOgu7fL&md5=088984701439c2c7abc478384f721861CAS | 19775188PubMed |
(b) M. Bakthadoss, G. Murugan, Eur. J. Org. Chem. 2010, 5825.
| Crossref | GoogleScholarGoogle Scholar |
(c) M. Bakthadoss, N. Sivakumar, Synlett 2011, 1296.
| Crossref | GoogleScholarGoogle Scholar |
(d) M. Bakthadoss, N. Sivakumar, A. Devaraj, Synthesis 2011, 611.
| Crossref | GoogleScholarGoogle Scholar |
(e) D. Basavaiah, M. Bakthadoss, S. Pandiaraju, Chem. Commun. 1998, 1639.
| Crossref | GoogleScholarGoogle Scholar |
(f) M. Bakthadoss, N. Sivakumar, Synlett 2009, 1014.
| Crossref | GoogleScholarGoogle Scholar |
(g) M. Bakthadoss, N. Sivakumar, G. Sivakumar, G. Murugan, Tetrahedron Lett. 2008, 49, 820.
| Crossref | GoogleScholarGoogle Scholar |
(h) M. Bakthadoss, N. Sivakumar, A. Devaraj, D. S. Sharada, Synthesis 2011, 2136.
| Crossref | GoogleScholarGoogle Scholar |
(i) D. Basavaiah, M. Bakthadoss, G. Jayapal Reddy, Synthesis 2001, 0919.
| Crossref | GoogleScholarGoogle Scholar |
[6] (a) R. Pathak, A. K. Roy, S. Batra, Synlett 2005, 848.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjtVyhu7o%3D&md5=f3f464890d70f369bb9e589aa4777c87CAS |
(b) V. Singh, S. Batra, Synthesis 2006, 63.
| Crossref | GoogleScholarGoogle Scholar |
(c) J. S. Yadav, B. V. S. Reddy, A. P. Sing, A. K. Basak, Synthesis 2008, 469.
| Crossref | GoogleScholarGoogle Scholar |
(d) G.-L. Zhao, J.-N. Huang, M. Shi, Org. Lett. 2003, 5, 4737.
| Crossref | GoogleScholarGoogle Scholar |
(e) S. Gowrisankar, H. S. Lee, J. M. Kim, J. N. Kim, Tetrahedron Lett. 2008, 49, 1670.
| Crossref | GoogleScholarGoogle Scholar |
(f) E. S. Kim, K. H. Kim, S. Park, J. N. Kim, Tetrahedron Lett. 2010, 51, 4648.
| Crossref | GoogleScholarGoogle Scholar |
(g) B. Das, J. Banerjee, G. Mahender, A. Majhi, Org. Lett. 2004, 6, 3349.
| Crossref | GoogleScholarGoogle Scholar |
(h) B. Das, K. Damodar, N. Bhunia, B. Shashikanth, Tetrahedron Lett. 2009, 50, 2072.
| Crossref | GoogleScholarGoogle Scholar |
[7] (a) R. Buchholz, H. M. R. Hoffmann, Helv. Chim. Acta 1991, 74, 1213.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXmtlWqsLg%3D&md5=091207439d80381e1580bfd785b262feCAS |
(b) S. Kawahara, A. Nakano, T. Esumi, Y. Iwabuchi, S. Hatakeyama, Org. Lett. 2003, 5, 3103.
| Crossref | GoogleScholarGoogle Scholar |
(c) S. Lee, S. Y. Moon, G.-S. Hwang, D. H. Ryu, Org. Lett. 2010, 12, 3234.
| Crossref | GoogleScholarGoogle Scholar |
