Streamlined access to 2,3-dihydropyrazino[1,2-a]indole-1,4-diones via Ugi reaction followed by microwave-assisted cyclization

Tetrahedron Letters

Volumn 50, Issue 39, 2009, Pages 5529-5531

  Tsirulnikov, Sergey ^a   Nikulnikov, Mikhail ^a   Kysil, Volodymyr ^b   Ivachtchenko, Alexandre ^b   Krasavin, Mikhail ^a  

^a Chemical Diversity Research Institute   (Russian Federation)

^b CHEMDIV INC   (United States)

Author keywords

Combinatorial chemistry; Isocyanide based multi component reactions; Microwave assisted synthesis; Post Ugi modifications

Indexed keywords

1H INDOLE 2 CARBOXYLIC ACID DERIVATIVE; 1H PYRAZOLE 3 CARBOXYLIC ACID DERIVATIVE; 2,3 DIHYDROPYRAZINO[1,2 A]INDOLE 1,4 DIONE; AMINE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; INDOLE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; CYCLIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICROWAVE RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; UGI MULTICOMPONENT REACTION;

EID: 68349127085     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.096     Document Type: Article

References (23)

1. Ugi I., Meyr R., Fitzer U., and Steinbrucker C. Angew. Chem. 71 (1959) 386-390
2. Hulme C., and Cherrier M.-P. Tetrahedron Lett. 40 (1999) 5295-5299
3. Tempest P., Ma V., Thomas S., Hua Z., Kelly M.G., and Hulme C. Tetrahedron Lett. 42 (2001) 4959-4962
4. Tempest P., Pettus L., Gore V., and Hulme C. Tetrahedron Lett. 44 (2003) 1947-1950
5. Banfi L., Basso A., Guanti G., Lecinska P., and Riva R. Org. Biomol. Chem. 4 (2006) 4236-4240
6. Umkehrer M., Kalinski C., Kolb J., and Burdack C. Tetrahedron Lett. 47 (2006) 3423-3426
7. Paulvannan K. Tetrahedron Lett. 40 (1999) 1851-1854
8. Ilyin A., Kysil V., Krasavin M., Kurashvili I., and Ivachtchenko A.V. J. Org. Chem. 71 (2006) 9544-9547
9. Akritopoulou-Zanze I., Whitehead A., Waters J.E., Henry R.F., and Djuric S.W. Org. Lett. 9 (2007) 1299-1302
10. Akritopoulou-Zanze I., Whitehead A., Waters J.E., Henry R.F., and Djuric S.W. Tetrahedron Lett. 48 (2007) 3549-3552
11. Akritopoulou-Zanze I., and Djuric S.W. Heterocycles 73 (2007) 125-147
12. Wu J., Yong J., and Wei-Min D. Synlett (2009) 1162-1166
13. Hulme C., Chapetta S., Griffith C., Lee Y.-S., and Dietrich J. Tetrahedron Lett. 50 (2009) 1939-1942
14. Erb W., Neuville L., and Zhu J. J. Org. Chem. 74 (2009) 3109-3115
15. Basso A., Banfi L., Guanti G., and Riva R. Org. Biomol. Chem. 7 (2009) 253-258
16. Nikulnikov M., Tsirulnikov S., Kysil V., Ivachtchenko A., and Krasavin M. Synlett (2009) 260-262
17. Nikulnikov, M.; Krasavin, M. IV International Conference on Multi-Component Reactions and Related Chemistry, 24-28 May, 2009, Ekaterinburg, Poster Abstract 18.
18. Boger D.L., Fink B.E., and Hedrick M.P. Bioorg. Med. Chem. Lett. 10 (2000) 1019-1020
19. Attia M.I., Witt-Enderby P.A., and Julius J. Bioorg. Med. Chem. 16 (2008) 7654-7661
20. Sinha S., Srivastava R., De Clercq E., and Singh R.K. Nucleosides, Nucleotides, Nucleic Acids 23 (2004) 1815-1824
21. Houston D.R., Synstad V.G., Eijsink V.G.H., Stark M.J.R., Eggleston I.M., and Van Aalten D.M.F. J. Med. Chem. 47 (2004) 5713-5720
22. ® equipment.
23. 4: C, 64.17; H, 5.60; N, 8.98; found: C, 64.22; H, 5.66; N, 9.04.