Synthesis of Dihydropyrrolo[2,1-a]isoquinolines by Regioselective [3+2] Cyclocondensation

Synlett

Volumn 1996, Issue 7, 1996, Pages 623-624

  Nemes, Péter ^a   Kajtár Peredy, Mária ^b   Scheiber, Pál ^a  

^a UNIVERSITY OF VETERINARY MEDICINE   (Hungary)

^b CTRL RES INSTITUTE FOR CHEMISTRY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003582634     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5542     Document Type: Article

References (16)

1. Grigg, R.; Gunaratne, H. Q. N.; Henderson, D.; Sridharan, V. Tetrahedron 1990, 46, 1599; Grigg, R.; Myers, P.; Somasunderam, A.; Sridharan, V. ibid. 1992, 48, 9735; Grigg, R.; Kennewell, P. Savic, V.; Sirdharan, V. ibid. 1992, 48, 10423. Grigg, R.; Montgomerry, J.; Somasunderam, A. ibid. 1992, 48, 10431.
2. Grigg, R.; Gunaratne, H. Q. N.; Henderson, D.; Sridharan, V. Tetrahedron 1990, 46, 1599; Grigg, R.; Myers, P.; Somasunderam, A.; Sridharan, V. ibid. 1992, 48, 9735; Grigg, R.; Kennewell, P. Savic, V.; Sirdharan, V. ibid. 1992, 48, 10423. Grigg, R.; Montgomerry, J.; Somasunderam, A. ibid. 1992, 48, 10431.
3. Grigg, R.; Gunaratne, H. Q. N.; Henderson, D.; Sridharan, V. Tetrahedron 1990, 46, 1599; Grigg, R.; Myers, P.; Somasunderam, A.; Sridharan, V. ibid. 1992, 48, 9735; Grigg, R.; Kennewell, P. Savic, V.; Sirdharan, V. ibid. 1992, 48, 10423. Grigg, R.; Montgomerry, J.; Somasunderam, A. ibid. 1992, 48, 10431.
4. Grigg, R.; Gunaratne, H. Q. N.; Henderson, D.; Sridharan, V. Tetrahedron 1990, 46, 1599; Grigg, R.; Myers, P.; Somasunderam, A.; Sridharan, V. ibid. 1992, 48, 9735; Grigg, R.; Kennewell, P. Savic, V.; Sirdharan, V. ibid. 1992, 48, 10423. Grigg, R.; Montgomerry, J.; Somasunderam, A. ibid. 1992, 48, 10431.
5. Tominaga, Y,; Shiroshita, Y.; Kurokawa, T.; Gotou, H.; Matsuda, Y.; Hosomi, A. J. Heterocyclic Chem. 1989, 26, 477.
6. Anderson, W. K.; Heider, A. R.; Raju, N.; Yucht, J. A. J. Med. Chem. 1988, 31, 2097.
7. Wasserman, H. H., Frechette, R.; Oida, T.; van Duzer, J. H. J. Org. Chem. 1989, 54, 6012.
8. Lösel, W. Chem.Ber 1988, 121, 547.
9. Lösel, W.; Roos, O.; Schnorrenberger, G. US. Patent 4694085, 1987; Chem. Abstr. 1988, 108, 204513.
10. Huisgen, R. Angew. Chem. 1963, 75, 604; Padwa, A. 1, 3-Dipolar Cycloaddition Reactions; Wiley: New York, 1984.
11. Huisgen, R. Angew. Chem. 1963, 75, 604; Padwa, A. 1, 3-Dipolar Cycloaddition Reactions; Wiley: New York, 1984.
12. Compound 1 must be handled carefully because of its particularly strong irritation contacting skin and slime tissues.
13. Harwood, H. J.; Johnson, T. B. J. Am. Chem. Soc. 1933, 55, 2555.
14. Vecchietti, V.; Clarke, G; D.; Colle, R.; Giardina, G.; Petrone, G.; Sbacchi, M. J. Med. Chem. 1991, 34, 2624.
15. Typical procedure for the preparation of compounds 3a-f. To a suspension of 2 g (7.24 mmole) of 1-chloromethyl-3,4-dihydroisoquinoline.HCl (1) and 30 ml of the ketone 3.79 g (30 mmole) of t-BuOK was added gradually at 0°C while stirring. The mixture was then stirred 2 hours at room temperature. The excess of the ketone was evaporated under reduced pressure. Then, 50 ml of water were added to the residue and the aqueous solution was extracted three times with 50 ml of diethyl ether. After drying over sodium sulfate and evaporation, the residue was subjected to flash column chromatography on silica gel using 20% ether in petroleum ether as eluant yielding a solid, which was recrystallized from isopropyl alcohol.
16. 2: C, 73.98; H, 6.99; N, 5.75. Found: C, 73.70, H, 6.97; N, 5.87.