53385-81-2

Upstream product

• 695-34-1 2-Amino-4-methylpyridine 
• 103-72-0 phenyl isothiocyanate 

Downstream Products

• 35466-43-4 N-phenyl-N'-(4-methylpyrid-2-yl)ureas 
• 100856-67-5 (7-Methyl-thiazolo[4,5-b]pyridin-2-yl)-phenyl-amine 
• 80291-22-1 VOCl₃(CH₃C₅NH₃NHCSNHC₆H₅) 
• 21242-21-7 1?(4?methylpyridin?2?yl)thiourea 
• 1266676-91-8 (4-methylpyridin-2-yl)-[4-(3-phenylisoxazol-5-yl)-thiazol-2-yl]-amine 
• 315705-36-3 [4-(3,4-dimethoxyphenyl)-thiazol-2-yl]-(4-methylpyridin-2-yl)-amine 
• 125859-37-2 Cu(bis{N-2-⁽⁴⁾picolyl-N'-(phenyl)thiourea})⁽²⁺⁾ 
• 103-84-4 Acetanilid 
• 1109168-42-4 4-hydroxy-4-methoxycarbonyl-2-(4-methyl-2-pyridylimino)-3,5-diphenylthiazolidine 
• 1109168-28-6 4-hydroxy-4-methoxycarbonyl-3-(4-methyl-2-pyridyl)-5-phenyl-2-phenyliminothiazolidine 

Relevant academic research and scientific papers

Molecular Conformation of N,N'-Diarylthioureas: an Assessment by 1H NMR and Infrared Spectroscopy

Several N,N'-dipyridyl- and N-phenyl-N'-pyridyl-thioureas were examined in different solvents at various temperatures by 1H NMR in order to study their conformational properties.The influence of concentration and the methyl substituent in the pyridine ring on the chemical shifts of the NH and pyridine groups was investigated.The observed chemical shifts are analysed in terms of the conformational properties of the molecules.Free energy barriers to the internal rotation about the C-N bonds have been determined.Infrared spectra have been measured to supplement the NMR studies.Intramolecular hydrogen bonding played a major role in the preferred conformation of pyridylthioureas.The data further revealed an interesting dynamic exchange phenomenon occuring in symmetric N,N'-dipyridylthioureas between two intramolecularly hydrogen bonded conformers.

Diversity-Oriented Synthesis of Thiazolidine-2-imines via Microwave-Assisted One-Pot, Telescopic Approach and Its Interaction with Biomacromolecules

In this work, a one-pot, telescopic approach is described for the combinatorial library of thiazolidine-2-imines. The synthetic manipulation proceeds smoothly via the reaction of 2-aminopyridine/pyrazine/pyrimidine with substituted isothiocyanates followed by base catalyzed ring closure with 1,2-dibromoethane to obtain thiazolidine-2-imines with broad substrate scope and high functional group tolerance. The synthetic strategy merges well with the thiourea formation followed by base catalyzed ring closure reaction for the thiazolidine-2-imine synthesis in a more modular and straightforward approach. The synthetic procedure reported herein represents a cleaner route toward thiazolidine-2-imines as compared to traditional methodologies. Moreover, the biological significance of combinatorially synthesized thiazolidin-2-imines has been investigated for their use as possible inhibitors for acetyl cholinesterase through molecular docking studies.

Micelle-Enabled One-Pot Guanidine Synthesis in Water Directly from Isothiocyanate using Hypervalent Iodine(III) Reagents under Mild Conditions

In this work, we developed a one-pot synthesis of guanidine directly from isothiocyanate using DIB (diacetoxyiodobenzene) as a desulfurizing agent under micellar conditions in water. Our optimization study revealed that the use of 1 % TPGS-750-M as a surfactant with NaOH as an additive base at room temperature can convert a variety of isothiocyanates and amines into corresponding guanidines in excellent yields (69–95 %). This synthetic process in water can be applied to prepare guanidine at gram-scale quantity. Our aqueous micellar medium also demonstrated high reusability as the reaction can be performed for several cycles without losing its efficiency. The reaction is metal-free, utilizes water as solvent and practical (room temperature and open flask).

2-aminothiazoles as therapeutic leads for prion diseases

2-Aminothiazoles are a new class of small molecules with antiprion activity in prion-infected neuroblastoma cell lines (J. Virol. 2010, 84, 3408). We report here structure-activity studies undertaken to improve the potency and physiochemical properties of 2-aminothiazoles, with a particular emphasis on achieving and sustaining high drug concentrations in the brain. The results of this effort include the generation of informative structure-activity relationships (SAR) and the identification of lead compounds that are orally absorbed and achieve high brain concentrations in animals. The new aminothiazole analogue (5-methylpyridin-2-yl)-[4-(3-phenylisoxazol-5-yl)-thiazol-2-yl]-amine (27), for example, exhibited an EC50 of 0.94 μM in prion-infected neuroblastoma cells (ScN2a-cl3) and reached a concentration of ～25 μM in the brains of mice following three days of oral administration in a rodent liquid diet. The studies described herein suggest 2-aminothiazoles as promising new leads in the search for effective therapeutics for prion diseases.

Fused polycyclic nitrogen-containing heterocycles : 1117. 4-Hydroxy-3-phenyl-2-(2-pyridylimino)-and 4-hydroxy-2-phenyl-3-(2-pyridyl) thiazolidines and related thiazolo[3,4-a]quinoxalines

The condensation of methyl phenylchloropyruvate with 1-phenyl-3-(2-pyridyl) thiourea and its 3-and 4-picolyl homologs affords the corresponding 4-hydroxythiazolidines, which react with o-phenylenediamine to give one of two possible thiazolo[3,4-a]quinoxalines containing the pyridyl-or picolylimine substituents at position 1. 3a-Hydroxy-3-phenylimino-1-(2-pyridyl)thiazolo[3,4- a]quinoxalin-4-(3H,5H)-one, which is a covalent hydrate of the final product, was isolated as an intermediate in this reaction.

One-pot synthesis of 5-arylidene-2-imino-4-thiazolidinones under microwave irradiation

A rapid and easy solvent free one-pot synthesis of 5-arylidene-2-imino-4- thiazolidinones by condensation of the thioureas with chloroacetic acid and an aldehyde under microwave-irradiation is described.

Structural, spectral and thermal studies of substituted N-(2-pyridyl)-N′-phenylthioureas

N-2-(3-picolyl)-N′-phenylthiourea, 3PicTuPh, monoclinic, P21/n, a = 7.617(2) b = 7.197(5), c = 22.889(5) ?, β = 94.63(4)°, V = 1250.7(1) ?3 and Z = 4; N-2-(4-picolyl)-N′-phenylthiourea, 4PicTuPh, triclinic, P-1, a = 7.3960(5), b = 7.

Synthesis and antimicrobial activity of some pyridinyliminothiazoline derivatives

The synthesis of some pyridinyliminothiazoline derivatives starting from N-pyridine-N′-phenyl thiourea and α-halogenoacetophenones is described. The chemical structures of the compounds were elucidated. The prepared compounds were tested for antimicrobial activity.

STUDIES ON HETEROCYCLIC COMPOUNDS. XXXIV. SYNTHESIS OF 2-SUBSTITUTED AMINOBENZOXAZOLES WITH NICKEL PEROXIDE

Oxidation of N-methyl (or phenyl)-N'-(4-methylpyrid-2-yl)thiourea (Ia, b) with nickel peroxide (Ni-PO) under reflux in benzene or acetonitrile afforded the corresponding ureas (IIa, b).N-(2-Hydroxy-5-methylphenyl)-N'-methylthiourea (IVa) was synthesized by the reaction of 2-amino-4-methylphenol (III) and methyl isothiocyanate in benzene under reflux.Howevwer, the reaction of III and phenyl isothiocyanate in benzene under reflux did not afford the thiourea (IVb) but IVb was obtained in ethanol at room temperature.NiPO oxidation of thioureas (IVa-f) in acetonitrile at room temperature afforded 2-substituted aminobenzoxazoles (VIIa-f) in good yields.The reaction mechanisms of Ni-PO and thioureas (Ia, b and IVa-f) are discussed.Keywords: - N-substituted N'-(4-methylpyrid-2-yl)thioureas; N-substituted N'-(4-methylpyrid-2-yl)ureas; N-(2-hydroxyphenyl) N'-substituted thioureas; 2-substituted aminobenzoxazoles; nickel peroxide; oxidative cyclization; 2-mercaptobenzoxazole; isothiocyanates