Synthesis and Heterocyclization of 1‐Aryl‐2‐methyl‐4‐oxo‐1, 4, 5, 6‐tetrahydropyridine‐3‐carboxylates. (21st March 2017)

• Record Type: Journal Article
• Authors: Sapijanskaitė, Birutė; Mickevičienė, Kristina; Kantminienė, Kristina; Belyakov, Sergey; Mickevičius, Vytautas
• Is Part Of: Journal of heterocyclic chemistry. Volume 54:Number 5(2017:Sep.)
• Page Start: 2605
• Page End: 2613
• Publication Date: 2017-03-21
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2857
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract : A series of novel isoxazole, dihydropyrazolone, and tetrahydropyridine derivatives were synthesized by the reaction of corresponding ethyl 1‐substituted aryl‐2‐methyl‐4‐oxo‐1, 4, 5, 6‐tetrahydropyridine‐3‐carboxylates with different hydrazines and hydroxylamine. Reaction of tetrahydropyridone with N, N ‐dimethylformamide dimethyl acetal provided 1‐(5‐chloro‐2‐methylphenyl)‐2‐[2‐(dimethylamino)ethenyl]‐4‐oxo‐1, 4, 5, 6‐tetrahydropyridine‐3‐carboxylate, which was cyclized into a bicyclic compound on treatment with ammonium acetate. The structures of all synthesized compounds were confirmed by IR, 1 H NMR, and 13 C NMR spectroscopy data. The structure of 5‐(5‐chloro‐2‐methylphenyl)‐4‐methyl‐2‐phenyl‐2, 5, 6, 7‐tetrahydro‐3 H ‐pyrazolo[4, 3‐c]pyridin‐3‐one was unambiguously assigned by means of X‐ray analysis data. Abstract : ∎∎∎