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Studies toward the synthesis of cinachyramine. An efficient route to 1,5-diazabicyclo[4.4.0]dec-5-enes
Journal article   Peer reviewed

Studies toward the synthesis of cinachyramine. An efficient route to 1,5-diazabicyclo[4.4.0]dec-5-enes

Olga V Barykina-Tassa and Barry B Snider
Tetrahedron letters, Vol.56(23), pp.3151-3154
06/03/2015
DOI: https://doi.org/10.1016/j.tetlet.2014.12.071
PMCID: PMC4472388
PMID: 26097260

Abstract

1,5-hydrogen shifts 1,5-diazabicyclo[4.4.0]dec-5-enes hydrogenation pyrido[1,2-a]pyridimines hydrazones
Hydrogenation (3 atm) of readily available pyrido[1,2-a]pyrimidines 10, 14, and 17 over 5% Rh/Al2O3 forms 1,5-diazabicyclo[4.4.0]dec-5-enes 9, 15, and 18 in >95% yield, providing a general route to this little-studied class of compounds. All attempts to form the tetrahydro-1,2,4-triazine moiety of cinachyramine (1) by rearrangement of amidinium dimethylhydrazone 8 using the procedures developed by Kamatori to convert hydrazone 3a to tetrahydro-1,2,4-triazine 4a were unsuccessful.

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