Protection, metalation, and electrophilic substitution of 5-methyl tetrazole

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3655-3658

  Huff, Bret E ^a   LeTourneau, Michael E ^a   Staszak, Michael A ^a   Ward, Jeffrey A ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029888757     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00654-5     Document Type: Article

References (22)

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15. Reaction of the dianion of unprotected 5-methyl tetrazole with electrophiles in THF was unsuccessful. However, we did not extensively investigate the possibility of reacting the dianion with electrophiles in the presence of additives such as HMPA or DMPU.
16. 5-Methyl tetrazole [4076-36-2] was purchased from Aceto Corporation.
17. For a report on the reaction of 5-methyl terazole with MeI under PTC conditions see: Osipova, T. F.; Ostrovskii, V. A.;, Koldobskii, G. I.; Erusalimskii, G. B. Zh. Org. Khim. 1984, 20, 398.
18. 4: C, 77.28; H, 5.56; N, 17.16. Found: C, 77.34; H, 5.45; N, 17.26.
19. Organocopper or organocerium reagents did not provide any yield enhancement in the reaction of 2-trityl-5-methyl tetrazole with cyclohexanecarboxaldehyde.
20. 4O: C, 77.75; H, 5.59; N, 12.95. Found: C, 77.53; H, 5.66; N, 13.14.
21. 13C NMR, and elemental analyses.
22. 4O: C, 57.08; H, 5.16; N, 29.55. Found: C, 56.83; H, 5.30; N, 29.46.