Homologation of 1-(benzyloxymethyl)-1H-tetrazole via lithiation

Synlett

Volumn , Issue 5, 1998, Pages 528-530

  Satoh, Yoshitaka ^a   Moliterni, John ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001501727     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1708     Document Type: Article

References (6)

1. De Lombaert, S.; Stamford, L. B.; Blanchard, L.; Tan, J.; Hoyer, D.; Diefenbacher, C. G.; Wei, D.; Wallace, E. M; Moscal, M.; Savage, P.; Jeng, A. Y. Bioorg. Med. Chem. Lett. 1997, 7, 1059-64, and references cited therein.
2. Satoh, Y.; Marcopulos, N. Tetrahedron Lett. 1995, 36, 1759-62.
3. Yokoyama, M.; Hirano, S.; Matsushita, M.; Hachiya, T.; Kobayashi, N.; Kubo, M.; Togo, H.; Seki, H. J. Chem. Soc., Perkin Trans, 1 1995, 1747-53. In this article, rigorous regiochemical assignment of 3 and 4 using a variety of NMR techniques was reported.
4. The PMB protected 5-lithiotetrazole undergoes decomposition with concomitant loss of gaseous nitrogen to afford N-PMB-cyanamide. The temperature required for this irreversible process appears to be dependent upon the size of the N-1 substituent. See ref. 2, footnote 10. See also: Raap, R. Can. J. Chem. 1971, 44, 791-2. It is also possible that the ether oxygen of the BOM group may be stabilizing the lithiotetrazole through internal coordination. Studies clarifying these aspects are underway.
5. Yi, K. Y.; Yoo, S-e. Tetrahedron Lett. 1995, 36, 1679-82.
6. For a general review of synthesis and chemistry of tetrazoles, see: Butler, R. N. Comprehensive Heterocyclic Chemistry II; Storr, R. C. Ed.; Elsevier: Oxford, 1996, Vol. 4, pp 905-1006.