Synthesis of Benzo[b]indeno[2,1-d]furanone Skeleton from Ninhydrin and Cyclohexane-1,3-dione Derivatives

Bulletin of the Korean Chemical Society

Volumn 24, Issue 12, 2003, Pages 1725-1726

  Na, Jeong Eun ^a   Kim, Jeong Mi ^a   Lee, Sangku ^b   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

Aromatization; Benzo b indeno 2,1 d furanone; Cyclohexane 1,3 dione; Iodine; Methanol

Indexed keywords

ANTIVIRUS AGENT; BENZO[B]INDENO[2,1 D]FURANONE; CYCLOHEXANE 1,3 DIONE DERIVATIVE; CYCLOHEXANE DERIVATIVE; FURANONE DERIVATIVE; IODINE; METHANOL; NINHYDRIN; UNCLASSIFIED DRUG; VANADIUM;

AROMATIZATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0345743665     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2003.24.12.1725     Document Type: Article

References (27)

1. Kim, J. M.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2003, 24, 1057.
2. The benzo[b]indeno[2,1-d]furanone skeleton have been known in some references, see: (a) Roth, H. J.; Kok, W. Arch. Pharmaz. 1976, 309, 81.
3. (b) Song, H. N.; Kim, H. S.; Kim, J. N. Bull. Korean Chem. Soc. 1999, 20, 631.
4. (c) Song, H. N.; Seong, M. R.; Lee, H. J.; Kim, J. N. Synth. Commun. 1999, 29, 2759.
5. (d) Poupelin, J.-P.; Saint-Ruf, G.; Perche, J.-C.; Roussey, J.-C.; Laude, B.; Narcisse, G.; Bakri-Logeais, F.; Hubert, F. Eur J. Med. Chem. 1980, 15, 253.
6. (e) Poupelin, J.-P.; Saint-Ruf, G.; Perche, J.-C.; Lacroix, R.; Uchida-Ernouf, G.; Narcisse, G.; Hubert, F. Eur. J. Med. Chem. 1979, 14, 171.
7. (a) Kotnis, A. S. Tetrahedron Lett. 1990, 31, 481.
8. (b) Horiuchi, C. A.; Fukunishi, H.; Kajita, M.; Yamaguchi, A.; Kiyomiya, H.; Kiji, S. Chem. Lett. 1991, 1921.
9. (c) Tamura, Y.; Yoshimoto, Y. Chem. Ind. 1980, 888.
10. (d) Mphahlele, M. J.; Pienaar, A.; Modro, T. A. J. Chem. Soc., Perkin Trans. 2 1996, 1455.
11. (e) Rao, P. N.; Cessac, J. W.; Kim, H. K. Steroids 1994, 59, 621.
12. (a) Schoop, A.; Greiving, H.; Gohrt, A. Tetrahedron Lett. 2000, 41, 1913.
13. (b) Kotnis, A. S. Tetrahedron Lett. 1991, 32, 3441.
14. (a) Hegde, S. G.; Kassim, A. M.; Ingrum, A. I. Tetrahedron Lett. 1995, 36, 8395.
15. (b) Hegde, S. G.; Kassim, A. M.; Kennedy, A. I. Tetrahedron 2001, 57, 1689.
16. (a) Yadav, J. S.; Reddy, B. V. S.; Sabitha, G.; Reddy, G. S. K. K. Synthesis 2000, 1532.
17. (b) Mphahlele, M. J.; Mogamisi, F. K.; Tsanwani, M.; Hlatshwayo, S. M.; Mampa, R. M. J. Chem. Research (S) 1999, 706.
18. Hirao, T.; Mori, M.; Ohshiro, Y. J. Org. Chem. 1990, 55, 358.
19. (a) Carotti, A.; Casini, G.; Ferappi, M.; Cingolani, G. M. J. Heterocyclic Chem. 1980, 17, 1577.
20. (b) Kaupp, G.; Naimi-Jamal, M. R.; Schmeyers, J. Chem. Eur. J. 2002, 8, 594.
21. 13C NMR spectra of cyclohexane-1,3-dione derivatives were very complex as reported and we did not assign them. (a) Im, Y. J.; Lee, C. G.; Kim, H. R.; Kim, J. N. Tetrahedron Lett. 2003, 44, 2987.
22. (b) Imashiro, F.; Maeda, S.; Takegoshi, K.; Terao, T.; Saika, A. J. Am. Chem. Soc. 1987, 109, 5213.
23. (c) Etter, M. C.; Urbanczyk-Lipkowska, Z.; Jahn, D. A.; Frye, J. S. J. Am. Chem. Soc. 1986, 108, 5871.
24. +, 100).
25. 2bc The reaction of 8 and methanol in the presence of acid catalyst (p-TsOH) afforded the methylated derivative 9 in 71% yield, Conversely, the conversion of 9 into 8 could be carried out in the presence of water and acid catalyst (conc. HCl) in 59% yield (Scheme 3). From the experiment we could propose the structure of 4a-c and 6a as described tentatively.
26. (a) Verhart, C. G. J.; Fransen, C. T. M.; Zwanenburg, B.; Chittenden, G. J. F. Recl. Trav. Chim. Pays-Bas. 1996, 115, 133.
27. (b) Rutherford, K.; Mamer, O.; Prokipcak, J.; Jobin, R. Can. J. Chem. 1966, 44, 2337.