Synthesis of 3-substituted 2-amino-1-hydroxy-1H-Indole-5, 6-dicarbonitriles

Chemistry of Heterocyclic Compounds

Volumn 48, Issue 3, 2012, Pages 427-435

  Filimonov, S I ^a   Chirkova, Zh V ^a   Sharunov, V S ^a   Abramov, I G ^a   Stashina, G A ^b   Firgang, S I ^b   Suponitsky, K Yu ^c  

^a YAROSLAVL STATE TECHNICAL UNIVERSITY   (Russian Federation)

^b N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

1 hydroxy 1H indole 5,6 dicarbonitriles; 2,1 benzisoxazoles; C nucleophi lic substitution; Phthalonitriles; Reductive cyclization

Indexed keywords

EID: 85027956161     PISSN: 00093122     EISSN: 15738353     Source Type: Journal    
DOI: 10.1007/s10593-012-1010-6     Document Type: Article

References (37)

1. M. Somei, Top. Heterocycl. Chem., 6, 77 (2006).
2. M. Somei, Adv. Heterocycl. Chem., 82, 101 (2002).
3. M. Somei, Heterocycles, 50, 1157 (1999).
4. R. M. Acheson, Adv. Heterocycl. Chem., 51, 110 (1990).
5. K. C. Nicolaou, A. A. Estrada, G. C. Freestone, S. H. Lee, and X. A.-Mico, Tetrahedron, 63, 6088 (2007).
6. B.-C. Chen, J. Hynes, Jr., C. R. Pandit, R. Zhao, A. P. Skoumbourdis, H. Wu, J. E. Sundeen, and K. Leftheris, Heterocycles, 55, 951 (2001).
7. M. Belley, E. Sauer, D. Beaudoin, P. Duspara, L. A. Trimble, and P. Dubé, Tetrahedron Lett., 47, 159 (2006).
8. J. Duflos, G. Dupas, and G. Queguiner, J. Heterocycl. Chem., 20, 1191 (1984).
9. D. Giomi and M. Cecchi, Tetrahedron, 58, 8067 (2002).
10. D. Giomi and M. Cecchi, J. Org. Chem., 68, 3340, (2003).
11. I. G. Abramov, M. V. Dorogov, S. A. Ivanovsky, A. V. Smirnov, and M. B. Abramova, Mendeleev Commun., 10, 78 (2000).
12. I. G. Abramov, A. V. Smirnov, S. A. Ivanovsky, M. B. Abramova, and V. V. Plakhtinskii, Heterocycles, 55, 1161 (2001).
13. I. G. Abramov, A. V. Smirnov, S. A. Ivanovsky, M. B. Abramova, V. V. Plakhtinskii, and M. S. Belysheva, Mendeleev Commun., 11, 80 (2001).
14. I. G. Abramov, A. V. Smirnov, S. A. Ivanovskii, M. B. Abramova, and V. V. Plakhtinskii, Khim. Geterotsikl. Soedin., 1219 (2000).
15. Chem. Heterocycl. Compd., 36, 1062 (2000).
16. I. G. Abramov, A. V. Smirnov, S. A. Ivanovsky, M. B. Abramova, and M. S. Belysheva, Khim. Geterotsikl. Soedin., 660 (2002).
17. Chem. Heterocycl. Compd., 38, 576 (2002).
18. S. A. Siling, S. V. Shamshin, A. B. Grachev, O. Yu. Tsiganova, V. I. Yuzhakov, A. V. Smirnov, I. G. Abramov, S. A. Ivanovsky, A. G. Vitukhnovsky, A. S. Averjushkin, and B. C. Lap, Oxid. Commun., 23, 481 (2000).
19. V. E. Maizlish, A. E. Balakirev, O. V. Shishkina, and G. P. Shaposhnikov, Zh. Obshch. Khim., 71, 274 (2001).
20. A. E. Balakirev, V. E. Maizlish, and G. P. Shaposhnikov, Zh. Obshch. Khim., 72, 336 (2002).
21. M. Makosza and K. Wojciechowski, Chem. Rev., 104, 2631 (2004).
22. O. Kaumanns, R. Appel, T. Lemek, F. Seeliger, and H. Mayr, J. Org. Chem., 74, 75 (2009).
23. M. V. Vlasov, Usp. Khim., 72, 764 (2003).
24. G. A. Artamkina, S. V. Kovalenko, I. P. Beletskaya, and O. A. Reutov, Usp. Khim., 59, 1288 (1990).
25. J. G. Zeevaart, C. J. Parkinson, and C. B. Koning, Tetrahedron Lett., 48, 3289 (2007).
26. M. Strauss and R. Torres, J. Org. Chem., 54, 756 (1989).
27. H. Suzuki, H. Koide, and T. Ogawa, Bull. Chem. Soc. Jpn, 61, 501 (1988).
28. Y. V. Il'ichev, M. A. Schwörer, and J. Wirz, J. Am. Chem. Soc., 126, 4581 (2004).
29. H. Stephensen and F. Zaragoza, Tetrahedron Lett., 40, 5799 (1999).
30. M. Belley, D. Beaudoin, P. Duspara, E. Sauer, G. St-Pierre, and L. A. Trimble, Synlett, 2991 (2007).
31. M. Makosza and A. A. Tomashewskij, J. Org. Chem., 60, 5425 (1995).
32. Z. Wrobel, Pol. J. Chem., 72, 2384 (1998).
33. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. 2, S1 (1987).
34. S. A. Ivanovsky, M. V. Dorogov, I. G. Abramov, and A. V. Smirnov, Russ. Pat. 2167855; Byull. Izobret. No. 12, 6 (2001).
35. C. Maurin, F. Bailly, and Ph. Cotelle, Tetrahedron, 60, 6479 (2004).
36. APEX2 and SAINT, Bruker AXS Inc., Madison, Wisconsin (2005).
37. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).