Tandem synthesis of functionalized tetrahydro-4aH-benzo[c]isoquino[1,2-t]pyrrolo[1,2-a][1,6]naphthyridines

Tetrahedron Letters

Volumn 49, Issue 45, 2008, Pages 6433-6436

  Yavari, Issa ^a   Karimi, Elham ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

3 Chloropentane 2,4 dione; Acetylenic ester; Isoquinoline; Tandem reaction

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ISOQUINOLINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 52249097401     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.095     Document Type: Article

References (16)

1. Mukaiyama T. Challenges in Synthetic Organic Chemistry (1990), Clarendon Press, Oxford
2. Ho T.-L. Tandem Organic Reactions (1992), John Wiley & Sons, New York
3. Ho T.-L. Tactics of Organic Synthesis (1994), John Wiley & Sons, New York
4. Serratosa F., and Xicart J. Organic Chemistry in Action: The Design of Organic Synthesis (1996), Elsevier, New York
5. Smith W.A., Bochkov A.F., and Caple R. Organic Synthesis: The Science behind the Art (1998), Royal Society of Chemistry, Cambridge, U.K.
6. Baguley P.A., and Walton J.C. J. Chem. Soc., Perkin Trans. 1 (1998) 2073
7. Schultz A.G., and Pettus L. J. Org. Chem. 62 (1997) 6855
8. Yavari I., Ghazanfarpour-Darjani M., Sabbaghan M., and Hossaini Z. Tetrahedron Lett. 48 (2007) 3749
9. Yavari I., Mokhtarporyani-Sanandaj A., and Moradi L. Tetrahedron Lett. 48 (2007) 6709
10. Yavari I., Mirzaei A., and Moradi L. Helv. Chim. Acta 89 (2006) 2825
11. Yavari I., Hossaini Z., and Sabbaghan M. Tetrahedron Lett. 47 (2006) 6037
12. 2 was added 0.24 ml of isoquinoline (2 mmol) dropwise at -10 °C over 5 min. The reaction mixture was then allowed to warm up to room temperature and stand for 2 h. The solvent was removed under reduced pressure, and the residue was purified by silica gel (Merck 230-240 mesh) column chromatography using 4:1 n-hexane-EtOAc mixture as eluent to afford the pure product. Compound 4a: yield: 0.57 g (89%); red powder, mp: 143-145 °C.
13. Burnett, A. M. N.; Johnson, C. K. Oak Ridge National Laboratory Report ORNL-6895, 1996.
14. Huisgen R., Morikawa M., Herbig K., and Brunn E. Chem. Ber. 100 (1967) 1094
15. Winterfeldt E., Schumann D., and Dillinger H.J. Chem. Ber. 102 (1969) 1656
16. Dillinger H.J., Fengler G., Schumann D., and Winterfeldt E. Tetrahedron 30 (1974) 2553-2561