Annulation of heterocyclic rings on aromatic templates: The quinone monoketal route

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 2881-2884

  Ciufolini, Marco A ^a   Dong, Qing ^a   Yates, Matthew H ^a   Schunk, Stefan ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029998929     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00424-8     Document Type: Article

References (19)

1. Alfred P. Sloan Foundation Fellow, 1994-1996
2. Review: Molinski, T. F. Chem. Rev. 1993, 93, 1825.
3. An interesting alternative for electrophilic introduction of nitrogen onto aromatic rings has been described by: Leblanc, Y.; Boudreault, N. J. Org. Chem. 1995, 60, 4268.
4. Barco, A.; Benetti, S.; Casolari, A.; Pollini, G. P.; Spalluto, G. Tetrahedron Lett. 1990, 31, 3039.
5. Example of this reaction (seemingly the sole recorded one): Foster, C. H.; Payne, D. A. J. Am. Chem. Soc. 1978, 100, 2834. Discussion of similar chemistry: Swenton, J. S., in: The Chemistry of Quinonoid Compounds; Patai, S., Ed.; John Wiley & Sons: New York, NY, 1988; Vol. 2, Part 2, pp. 899-962.
6. Example of this reaction (seemingly the sole recorded one): Foster, C. H.; Payne, D. A. J. Am. Chem. Soc. 1978, 100, 2834. Discussion of similar chemistry: Swenton, J. S., in: The Chemistry of Quinonoid Compounds; Patai, S., Ed.; John Wiley & Sons: New York, NY, 1988; Vol. 2, Part 2, pp. 899-962.
7. 2CO.
8. 2CO.
9. Methylation of tert-butyl hydroquinone was quite selective for the less hindered OH; but the 2-methyl analogue reacted with almost no selectivity, necessitating a painstaking separation. Consequently, we focused on intermediates in the tert-butyl series to explore further transformations.
10. Obtained from cis -2-butene-1-4-diol and phthalimide by the Volante modification (Volante, R. P. Tetrahedron Lett. 1981, 22, 3119) of the Mitsunobu reaction (Mitsunobu, O. Synthesis 1981, 1), followed by hydrazinolysis.
11. Obtained from cis -2-butene-1-4-diol and phthalimide by the Volante modification (Volante, R. P. Tetrahedron Lett. 1981, 22, 3119) of the Mitsunobu reaction (Mitsunobu, O. Synthesis 1981, 1), followed by hydrazinolysis.
12. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399.
13. The more acidic PCC (Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 16, 2650) caused cleavage of the dimethyl ketal and oxidation of the aromatic ring to a quinone.
14. We thank Dr. Larry Alemany, of this Department, for his valuable assistance with these measurements.
15. All computational work was carried out with the HYPERCHEM 4.0® package, available from Hypercube, Inc., Waterloo, Ontario, and running on a Windows® based Pentium/100 PC system.
16. Cf. Seebach, D.; Golinski, J. Helv. Chim. Acta 1981, 64, 1413.
17. For similar reactions see: (a) Parker, K. A.; Kang, S.-K. J. Org. Chem. 1980, 45, 1218;
18. (b) Parker, K. A.; Coburn, C. A.; Johnson, P. A.; Aristoff, P. J. Org. Chem. 1992, 57, 5547.
19. 2= 1.8 Hz); 3.91 (m, 2H); 3.65 (s, 3H); 3.35 (s, 3H); 3.16 (t, 2H J=7.3 Hz); 3.01 (s, 3H); 2.70 (m, 2H); 2.23 (m, 1H), 1.64 (m, 1H); 1.40 (m, 1H); 1.14 (s, 9H). 199.5; 157.1; 152.2; 142.3; 98.7; 61.2; 58.8; 54.0; 53.4; 52.5; 49.6; 48.9; 40.7; 35.1; 30.0; 29.5. 355. 18 low-melting s., 7.75 (m, 4H); 6.39 (s, 1H); 4.51 (br. d, 2H); 3.90 (m, 2H); 3.70 (s, 3H); 3.45 (s, 3H); 3.30 (m, 2H); 3.09 (s, 3H); 2.10 (m, 1H); 1.75 (m, 1H); 1.65 (m, 1H); 1.25 (s, 9H). 20 oil 5.85 (bs, 1H); 4.55 (bs, 1H); 4.00 (m, 1H); 3.72 (s, 3H); 3.42 (s, 3H); 3.18 (m, 2H); 3.08 (s, 3H); 2.55 (m, 2H); 1.85 (m, 1H); 1.62 (bs, 1H), 1.20 (s, 9H); 99 (m, 1H). 336. 21: oil 9.68 (s, 1H); 6.70(s, 1H); 5.30 (s, 1H); 4.32 (m, 1H); 3.86 (s, 3H); 3.60-3.27 (br. m, 5H); 2.15 (br. m, 1H); 1.59 (br. m, 1H); 1.37 (s, 9H).