Synthesis of 3‐dialkylaminomethyl‐5‐methyl‐4‐substituted‐1 H ‐pyrazoles. Selective functionalization of one methyl group  via n ‐nitration of 3,5‐dimethyl‐4‐substituted‐1 H ‐pyrazoles | Zendy

Lammers H. | Zendy; Vollinga R. | Zendy; Zandbergen P. | Zendy; CohenFernandes P. | Zendy; Habraken C. L. | Zendy

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Synthesis of 3‐dialkylaminomethyl‐5‐methyl‐4‐substituted‐1 H ‐pyrazoles. Selective functionalization of one methyl group via n ‐nitration of 3,5‐dimethyl‐4‐substituted‐1 H ‐pyrazoles

Author(s) -

Lammers H.,

Vollinga R.,

Zandbergen P.,

CohenFernandes P.,

Habraken C. L.

Publication year - 1995

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570320309

Subject(s) - chemistry , nitration , substituent , acetonitrile , nitro , surface modification , medicinal chemistry , inert , organic chemistry , combinatorial chemistry , alkyl

Treatment of 4‐substituted 3,5‐dimethyl‐1‐nitro‐1 H ‐pyrazoles 1 and 10a‐c with secondary amines in acetonitrile, in the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU), affords the novel dialkyl‐aminomethyl‐1 H ‐pyrazoles 5, 6, 7, 8, 11a‐c, 12a‐c and 13a‐c in good to excellent yields. In this way one of the, in general, inert methyl groups of 3,5‐dimethyl‐4‐substituted‐1 H ‐pyrazoles is functionalized creating a new synthetic route to azoles containing a coordinating substituent.

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