Parham-type cyclization and nucleophilic addition-N-acyliminium ion cyclization sequences for the construction of the isoquinoline nucleus

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6193-6196

  Collado, M Isabel ^a   Sotomayor, Nuria ^a   Villa, María Jesús ^a   Lete, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLIZATION; DRUG CONFORMATION; STRUCTURE ANALYSIS;

EID: 0030593585     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01321-4     Document Type: Article

References (16)

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2. (b) Snieckus, V. Pure Appl. Chem. 1994, 66, 2155-2158.
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4. 3. Hendi, M. S.; Natalie, Jr., K. J.; Hendi, S. B.; Campbell, J. A; Greenwood, T. D.; Wolfe, J. F. Tetrahedron Lett. 1989, 30, 275-278.
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6. 5. (a) Lete, E.; Egiarte, A.; Sotomayor, N.; Vicente, T.; Villa, M. J. Synlett, 1993, 41-43.
7. (b) Collado, M. I.; Lete, E.; Sotomayor, N.; Villa, M. J. Tetrahedron 1995, 51, 4701-4710.
8. (c) Lete, E.; Collado, M. I.; Sotomayor, N.; Vicente, T.; Villa, M. J. J. Heterocycl. Chem. 1995, 32, 1751-1758.
9. 6. The requisite imide substrates 1a-d were prepared by condensation of 3,4-dimethoxyphenethylamine with cyclic anhydrides, while imides 1f, 1h, and 1j were prepared by the Mitsunobu reaction of 3,4-dimethoxyphenethyl alcohol and imides. Reaction of imides 1d, 1f, and 1h with LDA/IMe yielded the 1e, 1g, and 1i, respectively. Treatment of these N-phenethylimides with ICl in glacial acetic acid produced the iodinated derivatives 2 in high yields (75-95%).
10. 7. (a) Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Academic Press: New York, 1988; vol. 32, pp. 271-339.
11. (b) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; vol. 2; pp. 1047-1082.
12. 13C NMR, and MS) data consistent with the depicted structures.
13. 9. Guiles, J. W.; Meyers, A. I. J. Org. Chem. 1991, 56, 6873-6878, and references therein.
14. 10. Kóbor, J.; Sohár, P. Fülöp, F. Tetrahedron 1994, 50, 4873-4886, and references therein.
15. 11. The regiochemistry of the nucleophilic additions to the carbonyl group of unsymmetrical imides was confirmed by performing NOESY experiments on the obtained products.
16. 12. Kano, S., Yuasa, Y.; Shibuya, S. Synth. Commun. 1985, 15, 883-889, and references therein.