87992-49-2

Upstream product

• 86796-01-2 2,2-dimethyl-N-phenyl-6-phenylimino-3,6-dihydro-2H-thiopyran-4-amine 
• 84260-83-3 6,6-Dimethyl-2-methylthio-5,6-dihydro-4H-thiopyran-4-on 
• 62-53-3 aniline 
• 84260-98-0 4-(2,2-Dimethyl-6-methylsulfanyl-2,3-dihydro-thiopyran-4-ylidene)-morpholin-4-ium; iodide 
• 84260-96-8 (2,2-Dimethyl-6-methylsulfanyl-2,3-dihydro-thiopyran-4-ylidene)-dimethyl-ammonium; iodide 
• 87992-42-5 C₁₉H₂₀N₂S*ClH 

Downstream Products

• 1094210-05-5 trans-2,2-dimethyl-6-methylthio-N,1-diphenyl-2,3-dihydropyridin-4(1H)-iminium iodide 
• 1094210-07-7 cis-2,2-dimethyl-6-methylthio-N,1-diphenyl-2,3-dihydropyridin-4(1H)-iminium iodide 

Relevant academic research and scientific papers

Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives

2-Substituted derivatives of the antihistaminic agents Bamipine, Diphenylpyraline and of their 1-phenyl analogues were tested for their antimycobacterial and H1-antagonistic activities. They are strong H1-receptor antagonists and also inhibit the growth of mycobacterials with a maximum MIC of 6.25 μg/mL against Mycobacterium tuberculosis H37Rv. H1-receptor antagonistic potency was slightly decreased by substitution in ring position 2 and distinctly diminished by N-aryl substitution. The antimycobacterial potency of Diphenylpyraline was in general increased by substitution in ring position 2, whereas only a few Bamipine derivatives showed markedly improved activity. A correlation between the two activities was not detected for those compounds.

Syntheses of 1-Substituted 4-Amino-2(1H)-pyridinethione by Dimroth-Reaction of 2,4-Diaminothiopyranylium Halogenides

4-Amino-2-alkylimino-2H-thiopyranes (5) and 4-amino-2-alkylaminothiopyranylium halogenides (4) resp. on heating in refluxing D M F A are rearranged in the presence of Na-ethylate to 1-alkyl-4-aminodihydro-2(1H)-pyridinethiones (2).Also 2-methylthiothiopyranylidenammonium iodides (6) and 2-methylthio-4H-thiopyrane-4-one (7) can be transformed into 1-substituted 2(1H)-pyridinethiones (2) by heating in prim. amines.On treatment with alkali, 4-dimethylaminothiopyranylium iodide (4a) is transformed into its base 5a and hydrolyzed to 8. 5a and 8 are rearranged to the pyridinethiones 2a and the tautomers 9 A, B.The structure of the rearranged pyridinethiones 2 was proved by the 1-phenylderivate 2a.Thus 4-methyl-3-penten-2-on reacts with phenylthiourea via the phenylimino-1,3-thiazine (14) to give 3-phenyl-2(1H)pyridinethione (15). 15 is transformed by the methylpyrimidine-pyridine-rearrangement to the 1-phenylpyridinethione 2a.The mechanism of the Dimroth-reaction of 2-alkylimino-2H-thiopyranes (5) and the stereochemistry of the 1-benzyl-6-phenyl-2(1H)-pyridinethiones 2 are discussed. - Keywords: Conformational analysis of benzyl phenyl 2(1H) pyridinethiones; Dimroth-reaction; Keto-enol-tautomerism of 1-substituted 4-hydroxy-2(1H)-pyridinethiones; 2-Methylthiothiopyranylidenammonium iodides and 2-methylthio-4H-thiopyrane-4-one, reaction with primary amines