94223-65-1Relevant articles and documents
SYNTHESIS OF CYCLOPENTANO-s-TRIAZOLES BY THE INTRAMOLECULAR RING TRANSFORMATION OF 1,3,4-OXADIAZOLES
Sasaki, Tadashi,Ohno, Masatomi,Ito, Eikoh,Asai, Koji
, p. 2703 - 2710 (2007/10/02)
Cyclopentano-s-triazoles were synthesized by intramolecular ring transformation starting from γ-keto-1,3,4-oxadiazoles 5 and 9.The required functionality for this intramolecular reaction was established by (i) the reaction of lithiated 2-methyl-1,3,4-oxadiazole 4 with the methyl enol ether of α-bromo ketones followed by hydrolysis; (ii) reductive amination of γ-ketones 5 and 9 to further reorganized hydrazide 7 and γ-amino-1,3,4-oxadiazole 9 with NaBH3CN; and (iii) pyrolysis of 7 and 9 at 280 deg C (5 mmHg) to the cyclopentano-s-triazoles 8 and 11.By the same treatment, the S-connected analogue 2 afforded the desired fused s-triazole 17.