Expeditious synthesis of chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines

Tetrahedron Letters

Volumn 54, Issue 18, 2013, Pages 2251-2254

  Bhowmik, Subhendu ^a   Kumar, Anil K S ^a   Batra, Sanjay ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

1,2,3,4 Tetrahydropyrrolo 1,2 a pyrazines; Amino acid; chiral; Furfurylamine; Reduction

Indexed keywords

NATURAL PRODUCT; PYRAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ONE POT SYNTHESIS;

EID: 84875712000     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.02.067     Document Type: Article

References (21)

1. A. Al-Mourabit, M.A. Zancanella, S. Tilvic, and D. Romo Nat. Prod. Rep. 28 2011 1229 1260 and references cited therein
2. G. Papeo, M.A. Gómez-ZuritaFrau, D. Borghi, and M. Varasi Tetrahedron Lett. 46 2005 8635 8638
3. Seredenin, S. B.; Voronina, T. A.; Beshimov, A.; Peresada, V. P.; Likhosherstov, A. M. RU 2,099,055, 1997; Chem. Abstr. 1998, 128, 290245j.
4. A.M. Likhosherstov, O.V. Filippova, V.P. Peresada, S.A. Kryzhanovskii, M.B. Vititnova, N.V. Kaverina, and K.M. Reznikov Pharm. Chem. J. 37 2003 6 9
5. Seredenin, S. B.; Voronina, T. A.; Likhosherstov, A. M.; Peresada, Y. P.; Molodavkin, G. M.; Halikas, J. A. U.S. 5,378,846, 1995; Chem. Abstr. 1995, 123, 83350w.
6. V.P. Peresada, O.S. Medvedev, A.M. Likhosherstov, and A.P. Skoldinov Khim. Farm. Zh. 21 1987 1054 1059 Chem. Abstr. 1988, 108, 68298g
7. T. Negoro, M. Murata, S. Ueda, B. Fujitani, Y. Ono, A. Kuromiya, M. Komiya, K. Suzuki, and J.-I. Matsumoto J. Med. Chem. 41 1998 4118 4129
8. Merla, B.; Christoph, T.; Oberboersch, S.; Schiene, K.; Bahrenberg, G.; Frank, R.; Kuehnert, S.; Schroeder, W. WO 2008046582, 2008; Chem. Abstr. 2008, 148, 472076a.
9. Merla, B.; Christoph, T.; Oberboersch, S.; Schiene, K.; Bahrenberg, G.; Frank, R.; Kuehnert, S.; Schroeder, W. WO 2008046581, 2008; Chem. Abstr. 2009, 148, 495982g.
10. Gahman, T. C.; Zhao, C.; Lang, H.; Massari, M. E. U.S. 20,090,062,253, 2009; Chem. Abstr. 2009, 150, 283093j.
11. Skoldinov, A. P.; Likhosherstov, A. M.; Peresada, V. P. Brit. UK Pat. Appl. 2,025,936, 1980, Chem Abstr. 1981, 93, 186406k.
12. Skoldinov, A. P.; Likhosherstov, A. M.; Peresada, V. P. Ger.Offen. 2,832,488, 1980; Chem. Abstr. 1980, 93, 46720h.
13. Skoldinov, A. P.; Likhosherstov, A. M.; Peresada, V. P. USSR 798,104, 1981; Chem. Abstr. 1981, 95, 7337k.
14. A.R. Katritzky, R. Jain, Y.-J. Xu, and P.J. Steel J. Org. Chem. 67 2002 8220 8223
15. Y. He, M. Lin, Z. Li, X. Liang, G. Li, and J.C. Antilla Org. Lett. 13 2011 4490 4493 Also refer to Li, G.; Rowland,G. B.; Rowland, E. B.; Antilla, J. C. Org. Lett. 2007, 9, 4065-4068.
16. A.S. Demir, N.T. Subasia, and E. Sahin Tetrahedron: Asymmetry 17 2006 2625 2631
17. A. Gualandi, L. Cerisoli, M. Monari, and D. Savoia Synthesis 2011 909 918
18. A few citations only A.S. Pilipenko, V.V. Mel'chin, I.V. Trushkov, D.A. Cheshkov, and A.V. Butin Tetrahedron 68 2012 619 627
19. T. Okada, K. Sakaguchi, T. Shinada, and Y. Ohfune Tetrahedron Lett. 52 2011 5744 5746 and references cited therein
20. T.A. Stroganova, A.V. Butin, V.K. Vasilin, T.A. Nevolina, and G.D. Krapivin Synlett 2007 1106 1108
21. A.V. Butin, T.A. Nevolina, V.A. Shcherbinin, I.V. Trushkov, D.A. Cheshkov, and G.D. Krapivin Org. Biomol. Chem. 8 2010 3316 3327