Pyrrole photooxidation. A pathway to bipyrrolic products

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6657-6660

  Wasserman, Harry H ^a   Power, Patricia ^a   Petersen, Anders K ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PHOTOOXIDATION; REACTION ANALYSIS;

EID: 0030576928     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01489-X     Document Type: Article

References (18)

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5. 4. Lightner, D. A.; Bisacchi, G. S.; Norris, R. D. J. Am. Chem. Soc. 1976, 98, 802-807; Lightner, D. A.; Pak, C.-S. J. Org. Chem. 1975, 40, 2726-2728; Lightner, D. A.; Norris, R. D. N. Engl. J. Med. 1974, 290, 1260; Lightner, D. A.; Crandall, D. C. Tetrahedron Lett. 1973, 953-956; Lightner, D. A.; Low, L. K. Chem. Commun. 1972, 625-626.
6. 4. Lightner, D. A.; Bisacchi, G. S.; Norris, R. D. J. Am. Chem. Soc. 1976, 98, 802-807; Lightner, D. A.; Pak, C.-S. J. Org. Chem. 1975, 40, 2726-2728; Lightner, D. A.; Norris, R. D. N. Engl. J. Med. 1974, 290, 1260; Lightner, D. A.; Crandall, D. C. Tetrahedron Lett. 1973, 953-956; Lightner, D. A.; Low, L. K. Chem. Commun. 1972, 625-626.
7. 4. Lightner, D. A.; Bisacchi, G. S.; Norris, R. D. J. Am. Chem. Soc. 1976, 98, 802-807; Lightner, D. A.; Pak, C.-S. J. Org. Chem. 1975, 40, 2726-2728; Lightner, D. A.; Norris, R. D. N. Engl. J. Med. 1974, 290, 1260; Lightner, D. A.; Crandall, D. C. Tetrahedron Lett. 1973, 953-956; Lightner, D. A.; Low, L. K. Chem. Commun. 1972, 625-626.
8. 4. Lightner, D. A.; Bisacchi, G. S.; Norris, R. D. J. Am. Chem. Soc. 1976, 98, 802-807; Lightner, D. A.; Pak, C.-S. J. Org. Chem. 1975, 40, 2726-2728; Lightner, D. A.; Norris, R. D. N. Engl. J. Med. 1974, 290, 1260; Lightner, D. A.; Crandall, D. C. Tetrahedron Lett. 1973, 953-956; Lightner, D. A.; Low, L. K. Chem. Commun. 1972, 625-626.
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10. 6. Wasserman, H. H.; Lipshutz, B. H. Reactions of Singlet Oxygen with Heterocyclic Systems. Chapter 9 In Singlet Oxygen, Wasserman, H. H.; Murray, R. W., Eds.; Academic: New York, 1979 pp 429-509.
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13. + 423.2136. Found 423.2131 (1 ppm).
14. 10. Fuhlhage, D. W.; VanderWerf, C. A. J. Am. Chem. Soc. 1958, 80, 6249-6254.
15. 11. Rapoport, H.; Holden, K. G. J. Am. Chem. Soc. 1962, 84, 635-642.
16. 12. de Mayo, P.; Reid, S. T. Chem. Ind. 1962, 1576-1577.
17. 13. The O-methylated derivatives 4,6,12a,b were readily prepared by treating the corresponding hydroxy pyrroles 3 with sodium hydride and dimethyl sulfate. However, in the reaction of the methyl (3a) and benzyl (3b) esters, both oxygen and nitrogen were methylated, forming N-methylpyrroles 12a and 12b, respectively. Only the t-butyl ester 3c could be methylated exclusively at oxygen to give pyrrole 6. Presumably the t-butyl group provides extra hindrance, preventing the nitrogen from being methylated under these conditions. An N,O-dimethylated derivative (4) could be obtained if higher temperatures were employed or if more than one equivalent of dimethyl sulfate was used.
18. 2=Bn, 96%