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Main pathways in reactions of lactim ethers with cyanoacetic acid hydrazide depend on the ring size of the starting lactim ether. Five-membered O-methylbutyrolactim produces pre-dominantly 3-amino-4-(pyrrolidin-2-ylidene)-4,5-dihydropyrazol-5-one, whereas condensation of six-and seven-membered lactim ethers (O-methylvalero-and O-methylcaprolactim, respectively) affords the corresponding polymethylenetriazoles as the major products.
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