Simple access to pentacyclic oxazinoisoquinolines via an unexpected transformation of aminomethylnaphthols

Tetrahedron Letters

Volumn 52, Issue 34, 2011, Pages 4440-4442

  Szatmári, István ^a   Fülöp, Ferenc ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

3,4 dihydroisoquinoline; Aminonaphthol; Mannich reaction; Microwave reaction

Indexed keywords

1 ALPHA AMINOBENZYL 2 NAPHTHOL; 1 AMINOMETHYL 2 NAPHTHOL; 1 AMINOMETHYL 2 NAPHTHOL HYDROCHLORIDE; 6,7 DIMETHOXY 3,4 DIHYDROISOQUINOLINE; ISOQUINOLINE DERIVATIVE; N BENZYL 1 AAMINOBENZYL 2 NAPHTHOL; NAPHTH[1,2 E][1,3]OXAZINO[2,3 A]ISOQUINOLINE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; HEATING; MANNICH REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME;

HUMAN ECHOVIRUS 1;

EID: 79960839038     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.074     Document Type: Article

References (21)

1. T.S. Kaufman Tetrahedron: Asymmetry 15 2004 1203
2. T.S. Kaufman Synthesis 2005 339
3. K.W. Bentley Nat. Prod. Rep. 22 2005 249
4. M. Chrzanowska, and M.D. Rozwadowska Chem. Rev. 104 2004 3341
5. I. Szatmári, L. Lázár, and F. Fülöp Tetrahedron Lett. 47 2006 3881
6. P.D. MacLeod, Z. Li, and C.-J. Li Tetrahedron 66 2010 1045
7. P.D. MacLeod, A. Reckling, and C.-J. Li Heterocycles 80 2010 1319
8. I. Szatmári, and F. Fülöp Synthesis 2011 745
9. M. Heydenreich, A. Koch, I. Szatmári, F. Fülöp, and E. Kleinpeter Tetrahedron 64 2008 7378
10. R.E. Valters, F. Fülöp, and D. Korbonits Adv. Heterocycl. Chem. 64 1995 251
11. H. Kessler, H. Oschkinat, G. Zimmerman, H. Möhrle, M. Biegholdt, W. Arz, and H. Förster Chem. Ber. 117 1984 702
12. I. Szatmári, A. Hetényi, L. Lázár, and F. Fülöp J. Heterocycl. Chem. 41 2004 367
13. M. Heydenreich, A. Koch, S. Klod, I. Szatmári, F. Fülöp, and E. Kleinpeter Tetrahedron 62 2006 11081
14. I. Szatmári, and F. Fülöp Curr. Org. Synth. 1 2004 155
15. 3: C, 79.41; H, 5.95; N, 3.31. Found: C, 79.15; H, 5.91, N, 3.37.
16. I. Szatmári, T.A. Martinek, L. Lázár, and F. Fülöp Tetrahedron 59 2003 2877
17. 3: C, 76.06; H, 6.09; N, 4.03. Found: C, 76.17; H, 6.12, N, 4.08.
18. M.H. Mosslemin, M.R. Nateghi, and R. Mohebat Monatsh. Chem. 139 2008 1247
19. Y. Dong, R. Li, J. Lu, X. Xu, X. Wang, and Y. Hu J. Org. Chem. 70 2005 8617
20. 2 = 30.9 min.
21. C. Cimarelli, A. Mazzanti, G. Palmieri, and E. Volpini J. Org. Chem. 66 2001 4759