Synthesis of 1,2,3,4-Tetrahydroisoquinolines

Journal of Organic Chemistry

Volumn 47, Issue 13, 1982, Pages 2638-2643

  Kashdan, David S ^a   Schwartz, John A ^a   Rapoport, Henry ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010385036     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00134a025     Document Type: Article

References (32)

1. Whaley, W. M.; Govindachari, T. R. Org. React. 1951, 6, 74.
2. Kametani, T.; Fukumoto, K.; Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Wakisaka, K. J. Chem. Soc. C, 1971 (1805).
3. Kametani, T.; Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Haga, S.; J. Heterocycl. Chem. 1974, 11, 1063.
4. Rice, K. C.; Brossi, A. J. Org. Chem. 1980, 45, 592.
5. Kametani, T.; Kigasawa, K.; Hiiragi, M.; Ishimaru, H. J. Chem. Soc. C 1971, 2632.
6. Wagner, D. P.; Rachlin, A. I.; Teitel, S. Synth. Commun. 1971, 1, 47, and references therein.
7. Buck, J. S. J. Am. Chem. Soc. 1933, 55, 2593.
8. Kindler, K.; Schrader, K. Justus Liebig's Ann. Chem. 1949, 564, 49.
9. Nakanishi, K.; Ohashi, M.; Kumasaki, S.; Koike, H. Bull. Chem. Soc. Jpn. 1961, 34, 533.
10. Klein, K. P.; Hauser, C. R. J. Org. Chem. 1967, 32, 1479.
11. Narashimhan, N. S.; Bhide, B. H. Tetrahedron Lett., 1968 (4159).
12. Ranade, A. C.; Mali, R. S.; Bhide, S. R.; Mehta, S. R. Synthesis, 1976 (123).
13. 8 200 mol % of methyl chloroformate gave a 73% yield of lactone 19. Monitoring the reaction by TLC showed that lactone formation was concomitant with chloro ester formation. Lactonization of chloro ester 15 may be facilitated by lithium chloride present in the reaction mixture or may be solely a thermal process (attempted GC purification of 15 at 180 °C yielded lactone 19). Similar results have been reported by Hinton, I. G. H.; Mann, F. G. J. Chem. Soc. 1959, 599.
14. Uemura, M.; Tokuyama, S.; Sakan, T. Chem. Lett. 1975, 1195.
15. Helfer, L. Helv. Chim. Acta 1924, 7, 945.
16. Attenburrow, J.; Cameron, A. F. B.; Chapman, J. H.; Evans, R. M.; Hems, B. A.; Jansen, A. B. A.; Walker, T. J. Chem. Soc. 1952, 1094.
17. Fatiadi, A. J. Synthesis, 1975 (65).
18. Rieke, R. D. Fortsch. Chem. Forschung. 1975, 59, 1.
19. Rieke, R. D.; Bales, S. E. J. Am. Chem. Soc. 1974, 96, 1755.
20. McEwen, W. E.; Cobb, R. L. Chem. Rev. 1955, 55, 511.
21. Popp, F. D.; Adv. Heterocycl. Chem. 1968, 9, 1.
22. Beak, P.; Reitz, D. B. Chem. Rev. 1978, 78, 275.
23. Fraser R. R.; Boussard, G.; Postescu, I. D.; Whiting, J. J.; Wigfield, Y. Y. Can. J. Chem. 1973, 51, 1109.
24. Lohmann, J. J.; Seebach, D.; Syfrig, M. A.; Yoshifujii, M. Angew. Chem., Int. Ed. Engl. 1981, 20, 128.
25. Seebach, D.; Yoshifuji, M. Helv. Chim. Acta 1981, 64, 643.
26. Meyers, A. I.; Hellring, S.; Ten Hoeve, W. Tetrahedron Lett. 1981, 22, 5115.
27. Scribner, R. M. Tetrahedron Lett. 1976, 3853.
28. Collins, D. J.; Hobbs, J. J. Aust. J. Chem. 1967, 20, 1413.
29. Shavel, J.; Morrison, G. C. U.S. Patent 3438 989; Chem. Abstr. 1969, 71, 22, 236.
30. Tedeschi, D. H. U.S. Patent 3 272 707; Chem. Abstr. 1966, 65, 20, 109.
31. Schenker, F.; Schmidt, R. A.; Williams, T.; Brossi, A. J. Heterocycl. Chem. 1971, 8, 665.
32. McDonald, R. N.; Reineke, C. E. Org. Synth. 1970, 50, 51.