Regioselective synthesis of nitrosoimidazoheterocycles using tert-butyl nitrite. 2015

Kamarul Monir, and Monoranjan Ghosh, and Sourav Jana, and Pallab Mondal, and Adinath Majee, and Alakananda Hajra
Department of Chemistry, Visva-Bharati (A Central University), Santiniketan 731235, India. alakananda.hajra@visva-bharati.ac.in.

A simple and practical method has been developed for the regioselective nitrosylation of imidazopyridines via C(sp(2))-H bond functionalization using tert-butyl nitrite under mild reaction conditions in a short time. A library of 3-nitrosoimidazopyridines with broad functionalities was synthesized in near quantitative yields. The present protocol is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D009573 Nitrites Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M Nitrite
D009603 Nitroso Compounds Organic compounds containing the nitroso (-N Compounds, Nitroso
D011725 Pyridines Compounds with a six membered aromatic ring containing NITROGEN. The saturated version is PIPERIDINES.
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013844 Thiazoles Heterocyclic compounds where the ring system is composed of three CARBON atoms, a SULFUR and NITROGEN atoms. Thiazole
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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