New substituted indene derivatives from bicyclic Baylis-Hillman acetate

Authors

  • Hassen AMRI Professor

DOI:

https://doi.org/10.13171/mjc.4.2.2015.12.02.10.25/amri

Abstract

A convenient protocol for the synthesis of highly functionalized indenes 4 has been developed. The coupling reaction of bicyclic Baylis-Hillman acetate 2 with nitroalkane salts in basic conditions led to the corresponding substituted indenes in good yields and high purity.

References

G. Majetich, J. M. Shimkus, J. Nat. Prod. 2010, 73, 284-298.

K. Kawazoe, M. Yamamoto, Y. Takaishi, G. Honda, T. Fujita, E. Sezik, E. Yesilada, Phytochemistry 1999, 50, 493-497.

A. N. Nicholson, P. A. Pascoe, C. Turner, C. R. Ganellin, P. M. Greengrass, A. F. Casy, A. D. Mercer, Br. J. Pharmacol. 1991, 104, 270-276.

T. Koike, Y. Hoashi, T. Takai, M. Nakayama, N. Yukuhiro, T. Ishikawa, K. Hirai, O. Uchikawa, J. Med. Chem. 2011, 54, 3436-3444.

R. Kolanos, U. Siripurapu, M. Pullagurla, M. Riaz, V. Setola, B. L. Roth, M. Dukat, R. A. Glennon, Bioorg. Med. Chem. Lett. 2005, 15, 1987-1991.

T. Oda, Y. So, Y. Sato, N. Shimizu, H. Handa, Y. Yasukochi, T. Kasahara, Mutat. Res. 2003, 534, 187-195.

M. R. Schneider, H. Ball, J. Med. Chem. 1986, 29, 75-79.

S. H. Mehdi, R. Hashim, R. M. Ghalib, M. F. C. Guedes da Silva, O. Sulaiman, S. Z. Rahman, V. Murugaiyah, M. M. Marimuthu, J. Mol. Struct. 2011, 1006, 318-323.

A. Korte, J. Legros, C. Bolm, Synlett 2004, 2397-2399.

T. Katoh, T. Akagi, C. Noguchi, T. Kajimoto, M. Node, R. Tanaka, M. Nishizawa, H. Ohtsu, N. Suzuki, K. Saito, Bioorg. Med. Chem. 2007, 15, 2736.

P.-C. Lee, H.-J. Lee, R. Kakadiya, K. Sanjiv, T.-L. Su, T.-C. Lee, Oncogene 2013, 32, 1144-1154.

N. Watanabe, H. Nakagawa, A. Ikeno, H. Minato, C. Kohayakawa, J.-I. Tsuji, Bioorg. Med. Chem. Lett. 2003, 13, 4317-4320.

K. Serge, G. K. Pantelis, P. Daniel, B. Francoise, V. D. V. Patrick, II Farmaco 1999, 54, 678-683.

X. Zhu, H. Tsuji, K. Nakabayashi, S.-I. Ohkoshi, E. Nakamura, J. Am. Chem. Soc. 2011, 133, 16342-16345.

H. G. Alt, A. Köppl, Chem. Rev. 2000, 100, 1205-1222.

C. Li, Y. Zeng, J. Wang, Tetrahedron Lett. 2009, 50, 2956–2959.

H. Kheira, P. Li, J. Xu, J. Mol. Cat. A: Chem. 2014, 391, 168-174.

E. J. Park, S. H. Kim, S. J. Chang, Am. Chem. Soc. 2008, 130, 17268–17269.

G. B. Bajracharya, N. K. Pahadi, I. D. Gridnev, Y. Yamamoto, J. Org. Chem.2006, 71, 6204-6210.

T. Takahashi, Y. Kuzuba, F. Kong, K. Nakajima, Z. Xi, J. Am. Chem. Soc.2005,127, 17188–17189.

K. Bahadur, S. Magar, Y. R. Lee, Org. Lett. 2013, 15, 4288-4291.

E. M. Coyanis, J. L. Panayides, M. A. Fernandes, C. B. Koning, A. L. Willem, J. Organomet. Chem. 2006, 691, 5222-5239.

X. Zhang, W. T. Teo, W. Rao, D.-L. Ma, C.-H. Leung, P. W. H. Chan, Tetrahedron Lett. 2014, 55, 3881–3884.

J. Shao, P. Hu, G. Hong, M. Fang, X. Li, X. Xu, Synlett 2014, 25, 1009–1013.

D. Basavaiah, B. S. Reddy, H. Lingam Tetrahedron 2013, 69, 1994-2003.

D. Eom, S. Park, Y. Park, T. Ryu, P. H. Lee, Org. Lett. 2012, 14, 5392-5395.

H. Kurouchi, H. Sugimoto, Y. Otani, T. Ohwada, J. Am. Chem. Soc. 2010, 132, 807–815.

Z. A. Khan, T. Wirth, Org. Lett. 2009, 11, 229–231.

C. D. Smith, G. Rosocha, L. Mui, R. A. Batey, J. Org. Chem. 2010, 75, 4716–4727.

X. Zhou, H. Zhang, X. Xie, Y. Li, J. Org. Chem. 2008, 73, 3958–3960.

Y. Kuninobu, Y. Nishina, M. Shouho, K. Takai, Angew. Chem. Int. Ed. 2006, 45, 2766-2768.

P. G. Gassman, J. A. Ray, P. G. Wenthold, J. Mickelson, W. J. Org. Chem. 1991, 56, 5143–5146.

Q. Hou, Z. Zhang, F. Kong, S. Wang, H. Wang, Z.-J. Yao, Chem. Commun. 2013, 49, 695-697.

X. Shi, C. Li, Org. Lett. 2013, 15, 1476-1479.

J. Zhao, D. A. Clark, Org. Lett. 2012, 14, 1668-1671.

C. S. Bryan, M. Lautens, Org. Lett. 2010, 12, 2754-2757.

T. Furuta, T. Asakawa, M. Iinuma, S. Fujii, K. Tnaka, T. Kan, Chem. Commun. 2006, 3648–3650.

F. W. Patureau, T. Besset, N. Kuhl, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2154-2156.

S. Taktouk, J. Ben Kraïem, H. Chaabane, J. Lebreton, H. Amri, Med. J. Chem. 2013, 2(5), 658-666.

A. R. Daniewski, J.Kiegiel, J. Org. Chem. 1988, 53, 5535-5535.

K. Samula, B. Cichy, Acta Pol. Pharm.1985, 42, 256; Chem. Abstr. 1986, 105, 171931v.

S. Taktouk, J. Ben Kraïem, H. Amri, Synth. Commun. 2013, 44, 2004-2011.

A. Chamakh, M. M’hirsi, J. Villieras, J. Lebreton, H. Amri, Synthesis 2000, 295–299.

J. Ben Kraïem, H. Amri, J. Soc. Chim.Tunisie 2011, 13, 35-39.

H. Kraïem, T. Turki, H. Amri, Synth. Commun. 2003, 33, 3261-3269.

F. Beji, J. Lebreton, J. Villiéras, H. Amri, Tetrahedron 2001, 57, 9959-9962.

A. Fray, J. Ben Kraïem, H. Amri, Med. J. Chem. 2014, 3(3), 907-915.

I. Yavari, L. Moradi, A. Mokhtarporyani-Sanandej, A. Mirzaei, Helvetica Chimica Acta 2007, 90, 392-394.

Downloads

Published

2015-04-12

Issue

Vol. 4 No. 2 (2015)

Section

Organic Chemistry

License

Authors who publish with this journal agree to the following terms:

    1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
    2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
    3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).