Synthesis of 1,2,3,4-Tetrahydroisoquinolines Containing Electron-Withdrawing Groups

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 4116-4119

  Quallich, George J ^a   Makowski, Teresa W ^a   Sanders, Andrew F ^a   Urban, Frank J ^a   Vazquez, Enrique ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000643429     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972184e     Document Type: Article

References (33)

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4. (b) Whaley, W. M.; Govindachari, T. R. Org. React. 1951, 6, 74-150.
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6. (b) Whaley, W. M.; Govindachari, T. R. Org. React. 1951 6, 151-190.
7. (a) Grethe, G.; Bradsher, C. K.; Dyke, S. F.; Fukumoto, K.; Kametani, T. K.; Kinsman, R. G.; McDonald, E. The Chemistry of Heterocyclic Compounds Isoquinolines Part 1; Wiley: New York, 1981.
8. (b) Kathawala, F. G.; Coppola, G. M.; Schuster, H. F.; Bunting, J. W.; Duarte, F. F.; Mathison, I. W.; Nair, M. D.; Popp, F. D.; Premila, M. S.; Solomons, W. E. The Chemistry of Heterocyclic Compounds Isoquinolines Part 2; Wiley: New York, 1990.
9. Larsen, R. D.; Reamer, R. A.; Corley, E. G.; Davis, P.; Grabowski, E. J. J.; Reider, P. J.; Shinkai, I. J. Org. Chem. 1991, 56, 6034-8.
10. Bunnett, J. F.; Zahler R. E. Chem. Rev. 1951, 49, 273.
11. (a) For copper(I)-promoted malonate coupling reaction with aryl halides, see: Setsune, J. Matsukawa, K.; Wakemoto, H.; Kitao, T. Chem. Lett. 1981, 367-70. (b) Aryl halide displacements by malonate without copper catalysis see: Quallich, G. J.; Morrissey, P. M. Synthesis 1993, 51-3 and references therein.
12. (a) For copper(I)-promoted malonate coupling reaction with aryl halides, see: Setsune, J. Matsukawa, K.; Wakemoto, H.; Kitao, T. Chem. Lett. 1981, 367-70. (b) Aryl halide displacements by malonate without copper catalysis see: Quallich, G. J.; Morrissey, P. M. Synthesis 1993, 51-3 and references therein.
13. (a) Bruggink, A.; McKillop, A. Angew, Chem., Int. Ed. Engl. 1974, 13, 340-1.
14. (b) Bruggink, A.; McKillop, A. Tetrahedron 1975, 31, 2607-19.
15. Recovered starting material was obtained with these bases.
16. Diethyl malonate also provided the desired product 6a (R = Et) along with the corresponding methyl ester 6a (R = Me) resulting from transesterification with sodium methoxide. Methyl esters are typically more crystalline than ethyl esters, as found here with melting points of 153°C vs 104°C, respectively.
17. Bromobenzene is converted to anisole in 95% yield with copper(I) bromide catalysis in methanol with sodium methoxide. Aalten, H. L.; Koten, G.; Grove, D. M.; Kuilman, T.; Piekstra, O. G.; Hulshof, L. A.; Sheldon, R. A. Tetrahedron 1989, 45, 5565-78.
18. Toluene or tetrahydrofuran as cosolvents prevented the reaction from proceeding.
19. (a) Lane, C. F. Chem. Rev. 1976, 76, 773-97.
20. (b) Firestone, R. A.; Harris, E. E.; Reuter, W. Tetrahedron 1967, 23, 943-55.
21. Brown, H. C.; Rao, B. C. J. Am Chem. Soc. 1960, 82, 681.
22. (a) Lane, C. F.; Myatt, H. L.; Daniels, J.; Hopps, H. B. J. Org. Chem. 1974, 39, 3052.
23. (b) Plesek, J.; Hermanek, S.; Petrina, A. Chem. Abstr. 1973, 79, 146061y.
24. Alane did not provide better conversion to the diol. Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1464-72.
25. Direct reduction of diacid 7c with lithium aluminum hydride afforded diol 8c; see the Experimental Section.
26. 4, flow rate 1 mL/min, 280 nm.
27. Cyclization of o-chloroethyl benzyl chloride with alkylamines was a precedented route to tetrahydroisoquinolines. Lusinchi, X.; Durand, S.; Delaby, R. Compt. Rend. 1959, 248, 426-8.
28. Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195-6.
29. Pilzey, J. S. Synthetic Reagents; Wiley: New York, 1983; Vol. 5, p 26.
30. (Trimethylsilyl)amine is known to disproportionate at ambient temperature into hexamethyldisilizane and ammonia. Wiberg, N.; Uhlenbrock, W. Ber. 1971, 104, 2643-45.
31. See the Experimental Section.
32. Toluene prevented gumming of 6a (R = Me) but was not essential for the corresponding bromo 6b or trifluoromethyl 6c derivatives.
33. US patent no. 3,314,963, 1967; Chem. Abstr. 1967, 108567n.