- Generation of a structurally diverse library through alkylation and ring closure reactions using 3-dimethylamino-1-(thiophen-2-yl)propan-1-one hydrochloride
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3-Dimethylamino-1-(thiophen-2-yl)propan-1-one hydrochloride (2), a ketonic Mannich base derived from 2-acetylthiophene, was used as a starting material in different types of alkylation and ring closure reactions with a view to generate a structurally diverse library of compounds. Compound 2 reacts with S-alkylated dithiocarbamic acid salts and aryl mercaptans to produce dithiocarbamates and thioethers, respectively. The dimethylamino moiety in compound 2 was exchanged with various aliphatic secondary and aromatic primary and secondary amines, whereas monocyclic NH-azoles such as pyrazole, imidazole, 1,2,4-triazole, and tetrazole were N-alkylated by compound 2. Ketones, pyrrole and indoles have been the substrates subjected to C-alkylation reactions by compound 2. Ring closure reactions of compound 2 with a suitable bifunctional nucleophile yielded pyrazolines, pyridines, 2,3-dihydro-1,5-1H-benzodiazepines, 2,3-dihydro-1,5-1H- benzothiazepine, pyrimido[1,2-a]benzimidazole and 4-hydroxypiperidine derivatives.
- Roman, Gheorghe
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supporting information
p. 70 - 80
(2013/06/27)
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- Microwave-assisted cross-coupling of 3-chloro-2-pyrazolines and 3-chloro-1-phenyl-1,4,5,6-tetrahydropyridazine with aryl boronic acids
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3-Chloro-1-phenyl-2-pyrazoline and 3-chloro-1-phenyl-1,4,5,6- tetrahydropyridazine were coupled with aryl boronic acids in good yields under microwave heating conditions (140°C, 5 min).
- Wang, Hong-Jun,Keilman, Jeffrey,Pabba, Chittari,Chen, Zhen-Jia,Gregg, Brian T.
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p. 2631 - 2634
(2007/10/03)
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