An efficient construction of nitrogen-containing heterocycles utilizing CN functional groups and its application to the synthesis of natural products

Yakugaku Zasshi

Volumn 131, Issue 7, 2011, Pages 1037-1046

  Kobayashi, Yusuke ^a  

^a MUKOGAWA WOMEN'S UNIVERSITY   (Japan)

Author keywords

Cyanoacetanilide; Epoxide arene cyclization; Glycocitlone; Houben Hoesch reaction; Quinolone; Viridicatin

Indexed keywords

ACETANILIDE DERIVATIVE; CYANOACETANILIDE; ELECTROPHILE; FUNCTIONAL GROUP; GLCYOCITLONE; GLYCINE DERIVATIVE; NATURAL PRODUCT; NITROGEN CONTAINING HETEROCYCLE; NITROGEN DERIVATIVE; UNCLASSIFIED DRUG; VIRIDICATIN;

ACYLATION; CHEMICAL REACTION; HOUBEN HOESCH REACTION; REVIEW; SYNTHESIS;

ACETANILIDES; BIOLOGICAL AGENTS; CYCLIZATION; ELECTRONS; HETEROCYCLIC COMPOUNDS; HYDROXYQUINOLINES; NITRILES; NITROGEN; ORGANIC CHEMISTRY PROCESSES; QUINOLONES;

EID: 79959998433     PISSN: 00316903     EISSN: 13475231     Source Type: Journal    
DOI: 10.1248/yakushi.131.1037     Document Type: Review

References (30)

1. Rappoport Z., "The Chemistry of the Cyano Group, " Interscience Publishers (J. Wiley & Sons), New York, 1970.
2. Nakao Y., Hiyama T., Yuki Gosei Kagaku Kyokai Shi, 65, 999-1008 (2007).
3. Kobayashi Y., Kamisaki H., Yanada R., Takemoto Y., Org. Lett., 8, 2711-2713 (2006).
4. Kobayashi Y., Kamisaki H., Takeda H., Yasui Y., Yanada R., Takemoto Y., Tetrahedron, 63, 2978-2989 (2007).
5. Kobayashi Y., Harayama T., Org. Lett., 11, 1603-1606 (2009).
6. Capell B. C., Olive M., Erdos M. R., Cao K., Faddah D. A., Tavarez U. L., Conneely K. N., Qu X., San H., Ganesh S. K., Chen X., Avallone H., Kolodgie F. D., Virmani R., Nabel E. G., Collins F. S., Proc. Natl. Acad. Sci. USA, 105, 15902-15907 (2008).
7. Cappelli A., Pericot Mohr G., Gallelli A., Rizzo M., Anzini M., Vomero S., Mennuni L., Ferrari F., Makovec F., Menziani M. C., De Benedetti P. G., Giorgi G., J. Med. Chem., 47, 2574-2586 (2004).
8. Luckner M., Mothes K., Tetrahedron Lett., 3, 1035-1039 (1962).
9. Mohammed Y. S., Luckner M., Tetrahedron Lett., 4, 1953-1958 (1963).
10. Austin D. J., Myers M. B., J. Chem. Soc., 1, 1197-1198 (1964).
11. Luckner M., Mohammed Y. S., Tetrahedron Lett., 5, 1987-1989 (1964).
12. Smith H. W., Rapoport H., J. Am. Chem. Soc., 91, 6083-6089 (1969).
13. Terada A., Yabe Y., Miyadera T., Tachikawa R., Chem. Pharm. Bull., 21, 807-810 (1973).
14. Arshad N., Hashim J., Kappe C. O., J. Org. Chem., 73, 4755-4758 (2008).
15. Taylor S. K., Org. Prep. Proced. Int., 24, 245-284 (1992).
16. Itai A., Toriumi Y., Tomioka N., Kagechika H., Azumaya I., Shudo K., Tetrahedron Lett., 30, 6177-6180 (1989).
17. Kobayashi Y., Katagiri K., Azumaya I., Harayama T., J. Org. Chem., 75, 2741-2744 (2010).
18. Kobayashi Y., Harayama T., Tetrahedron Lett., 50, 6665-6667 (2009).
19. Kobayashi Y., Nakatani T., Tanaka R., Okada M., Torii E., Harayama T., Kimachi T., Tetrahedron, 67, 3457-3463 (2011).
20. Spoerri P. E., DuBois A. S., Org. React., 5, 387-412 (1949).
21. Sato Y., Yato M., Ohwada T., Saito S., Shudo K., J. Am. Chem. Soc., 117, 3037-3043 (1995).
22. Nakamura S., Sugimoto H., Ohwada T., J. Org. Chem., 73, 4219-4224 (2008).
23. The Cambridge Crystallographic Data Centre, "CCDC763341 (21) and CCDC763342 (27). ": (http://www.ccdc.cam.ac.uk/), cited 4 May, 2011.
24. Mekhalfia A., Mutter R., Heal W., Chen B., Tetrahedron, 62, 5617-5625 (2006).
25. Ito C., Kondo Y., Wu T.-S., Furukawa H., Chem. Pharm. Bull., 48, 65-70 (2000).
26. Barr S. A., Boyd D. R., Sharma N. D., Loke P. L., Heterocycles, 79, 831-850 (2009).
27. Marson C. M., Tetrahedron, 48, 3659-3726 (1992).
28. Selvi S., Perumal P. T., Org. Prep. Proc. Int., 33, 194-198 (2001).
29. Meth-Cohn O., Rhouati S., Tarnowski B., Robinson A., J. Chem. Soc., Perkin Trans. 1, 1537-1543 (1981).
30. Adams D. R., Adams C., Synth. Commun., 20, 469-475 (1990).