A facile preparation of pyrrolo[3,4-b]indoles

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8611-8614

  Daly, Kevin ^a   Nomak, Rana ^a   Snyder, John K ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CYCLIC POTENTIOMETRY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030809931     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10312-4     Document Type: Article

References (32)

1. For reviews: (a) Erfanian-Abdoust, H.; Pindur, U. Chem. Rev. 1989, 89, 1681-1689.
2. (b) Pindur, U. Adv. Nitrogen Heterocycl. 1995, 1, 121-172.
3. For a review: (a) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P. Acc. Chem. Res. 1984, 17, 35-41. For an example since then:
4. (b) Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242-2248.
5. Gribble, G. W.; Keavy, D. J.; Davis, D. A.; Saulnier, M. G.; Pelcman, B.; Barden, T. C.; Sibi, M. P. Olson, E. R.; BelBruno, J. J. J. Org. Chem. 1992, 57, 5878-5891, and references therein.
6. Moody, C. J.; Rahimtoola, K. F.; Porter, B.; Ross, B. C. J. Org. Chem. 1992, 57, 2105-2114.
7. (a) Sha, C.-K.; Chuang, K.-S.; Young, J.-J. J. Chem. Soc., Chem. Comm. 1984, 1552-1554.
8. (b) Sha, C.-K.; Chuang, K.-S.; Wey, S.-J. J. Chem. Soc., Perkin Trans. I 1987, 977-980.
9. Sha, C.-K.; Yang, J.-F. Tetrahedron 1992, 48, 10645-10654.
10. For a review of iso-condensed heteroaromatic pyrroles including 2,4-dihydropyrrolo[3,4-b]indoles: (a) Sha, C.-K. Adv. Nitrogen Heterocycl. 1996, 2, 147-178. Since this review:
11. (b) Jeevanandam, A.; Srinivasan, P. C. J. Chem. Soc., Perk. Trans. I 1995, 2663-2665.
12. (c) Pelkey, E. T.; Chang, L.; Gribble, G. W. J.C.S., Chem. Comm. 1996, 1909-1910.
13. (a) Benson, S. C.; Palabrica, C. A.; Snyder, J. K. J. Org. Chem. 1987, 52, 4610-4614. The yield of the cycloaddition of indole with 2 to give 3a has now been optimized to 95%. For the related reaction of N-methylindole with 2:
14. (b) Seite, G.; Kaempchen, T. Arch. Pharm. (Weinheim) 1976, 309, 679-681.
15. Intramolecular cycloadditions with tethered alkynes were successful: Benson, S. C. PhD Dissertation, Boston University, 1992.
16. (a) Haider, N. Acta Chim. Slov. 1994, 41, 205-217.
17. (b) Haider, N.; Wanko, R. Heterocycles 1994, 38, 1805-1811.
18. Pyridazine ring contraction using zinc reductions: (a) Besford, L. S.; Bruce, J. M. J. Chem. Soc. 1964, 4037-4044.
19. (b) Bach, N. J.; Kornfeld, E. C.; Jones, N. D.; Chaney, M. O.; Dorman, D. E.; Paschal, J. W.; Clemens, J. A.; Smalstig, E. B. J. Med. Chem. 1980, 23, 481-491.
20. Boger, D. L.; Coleman, R. S.; Panek, J. S.; Yohannes, D. J. Org. Chem. 1984, 49, 4405-4409.
21. Boger, D. L.; Patel, M. J. Org. Chem. 1988, 53, 1405-1415.
22. 4, and then the solvent removed in vacuo. Flash chromatography on silica gel provided the desired pyrroloindole.
23. Seitz had also reported similar ring-opening in the reaction of indole with 3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine: Seitz, G.; Mohr, R. Chem. Zeit. 1987, 111, 81-82. N-Tosylindole also produce the analogous ring-opened 5 upon reaction with 2: ref. 9.
24. The ring contraction is thought to proceed via reduction to the 1,4-dihydropyridazine, which is reductively cleaved to the aminoaldimine followed by reclosure with subsequent loss of ammonia to produce the pyrrole, ref. 11a, also: (a) Haddlesey, D. I.; Mayer, P. A.; Szinai, S. S. J. Chem. Soc. 1964, 5269-5274,
25. (b) Lund, H. Acta Chem. Scand. 1967, 21, 2525-2543.
26. (c) Lund, H.; Jensen, E. Th. Acta Chem. Scand. 1970, 24, 1867-1877.
27. Electrolysis: 2 mA for 21 hr at rt; supporting electrolyte was TBAPF (0.1M).
28. 2 (5 mM 3b) with TBAPF as supporting electrolyte (0.1 M), -78 °C, sweep rate 0.0125 V/s. The return oxidation peaks are not observed if HOAc is added.
29. (a) Starowieyski, K. B.; Pasynkiewicz, S.; Sporzynski, A.; Wisniewska, K. J. Organomet. Chem. 1976, 117, C1-C3. For related reactions of triethylaluminum with esters:
30. (b) Baba, Y. Bull. Chem. Soc. Jpn. 1968, 41, 1022-1023.
31. Sha, C.-K.; Yang, J.-F.; Chang, C.-J. Tetrahedron Lett. 1996, 37, 3487-3488.
32. Carpino, L. A.; Barr, D. E. J. Org. Chem. 1966, 31, 764-767. Tetrahedron Letters, Vol. 38, No. 50, pp. 8615-8618, 1997