Triazole phosphonates. Electrophilic substitution of 1‐substituted‐1 H ‐1,2,4‐triazoles  via  lithiated triazole intermediates | Zendy

Anderson D. Keith | Zendy; Sikorski James A. | Zendy; Reitz David B. | Zendy; Pilla Linda T. | Zendy

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Triazole phosphonates. Electrophilic substitution of 1‐substituted‐1 H ‐1,2,4‐triazoles via lithiated triazole intermediates

Author(s) -

Anderson D. Keith,

Sikorski James A.,

Reitz David B.,

Pilla Linda T.

Publication year - 1986

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570230457

Subject(s) - chemistry , electrophile , metalation , electrophilic substitution , alkyl , triazole , medicinal chemistry , 1,2,3 triazole , stereochemistry , combinatorial chemistry , organic chemistry , catalysis

The metalation chemistry of several 1‐substituted‐1 H ‐1,2,4‐triazoles has been investigated. When various alkyl groups were incorporated in the 1‐position, lithiation proceeded exclusively at C‐5. The 1‐trityl‐, 1‐methyl‐, and 1‐benzyl‐5‐lithio‐1,2,4‐triazoles were stable at −78° and reacted cleanly with a variety of electrophiles. The 1‐benzyl and 1‐methyl derivatives were synthetically more versatile and could be successfully utilized to prepare several examples of the previously unknown 1,2,4‐triazol‐5‐yl phosphonates.

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