A practical synthesis of ethyl 1,2,4‐triazole‐3‐carboxylate and its use in the formation of chiral 1′,2′‐ seco ‐nucleosides of ribavirin | Zendy

Vemishetti Purushotham | Zendy; Leiby Robert W. | Zendy; Abushanab Elie | Zendy; Panzica Raymond P. | Zendy

Premium

A practical synthesis of ethyl 1,2,4‐triazole‐3‐carboxylate and its use in the formation of chiral 1′,2′‐ seco ‐nucleosides of ribavirin

Author(s) -

Vemishetti Purushotham,

Leiby Robert W.,

Abushanab Elie,

Panzica Raymond P.

Publication year - 1988

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.5570250253

Subject(s) - chemistry , carboxylate , amide , alkylation , ribavirin , hydrochloride , 1,2,4 triazole , organic chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry , catalysis , biochemistry , genotype , gene

A practical and efficient synthesis of ethyl 1,2,4‐triazole‐3‐carboxylate ( 6a , R' = H) from ethyl carboethoxyformimidate hydrochloride ( 7 ) is described. Alkylation of this heterocycle with the chloromethyl ethers of 1,3‐ O ‐dibenzylbutane‐1,2 R ,3 S ‐triol ( 8a ) and 1,3,4‐ O ‐tribenzylbutane‐1,2 R ,3 S ,4‐tetrol ( 8b ), followed by conversion of the ester function to the amide and deprotection, furnished the chiral 1′,2′‐ seco ‐nucleosides of ribavirin, 11a and 11b , respectively.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research