- Multicomponent Reactions with Cyclic Tertiary Amines Enabled by Facile C?N Bond Cleavage
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A novel and catalyst-free multicomponent reaction with cyclic tertiary amines, electron-deficient aryl halides or heteroaromatic halides, and Na2S enabled by facile C?N bond cleavage of the cyclic tertiary amines was developed. This direct and operationally simple method can be applied with a wide range of functional groups and provides an efficient and rapid approach to potentially drug-like products containing amine, azaarene, thioether, or phenol ether functionalities in good to excellent yields. The utility of this method was demonstrated by the rapid synthesis of the analgesic ruzadolane.
- Zhu, Qiming,Yuan, Qinghe,Chen, Mingwei,Guo, Mengping,Huang, Hanmin
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- Arylamine alkyl sulfide compound with structure similar to ruzadolane and preparation method of compound
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Provided are an arylamine alkyl sulfide compound with the structure similar to ruzadolane and a preparation method of the compound. The compound is obtained by adding Ar-X1, a compound shown as a general formula III, Ar-X2 and a sulfur source into solvent to completely react under heating according to a reaction equation (1), or the compound is obtained by adding Ar-X1, the compound shown as the general formula III and Ar-SM into the solvent to completely react under heating according to a reaction equation (2). The method is easy to operate, efficient and mild in reaction condition, and all the used reagents are low in price, easy to obtain, high in safety and suitable for industrialized mass production.
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Paragraph 0100; 0101
(2016/10/10)
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- Novel aminoalkylthio derivatives of triazolopyridine or triazoloquinoline, the processes for their preparation, and drugs, useful especially as analgesics, in which they are present
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The present invention relates to novel compounds corresponding to the formula: STR1 in which: n represents an integer between 1 and 8 and optimally 2 or 3; (CH2)n --N can also form a ring or a heterocycle, for example having 5 to 7 atoms and preferably 6 atoms; R1 and R2 can represent hydrogen or a lower alkyl having 1 to 5 carbon atoms or can form, together with the nitrogen, a ring such as pyrrolidine, piperidine, morpholine, thiomorpholine, phenyltetrahydropyridine, piperazine or piperazine N-substituted by an alkyl, a phenyl or a heterocycle; in the case of the phenyltetrahydropyridines and the phenylpiperazines or heteroarylpiperazines, the phenyl or the heterocycle may or may not be substituted by halogens or methoxy, thiomethyl, hydroxyl, nitro, amino, cyano, lower alkyl, trifluoromethyl or trichloromethyl groups; and R3, R4 and R5 can represent hydrogen, a lower alkyl, a hydroxyalkyl or hydroxybenzyl group, a halogen, a trifluoromethyl, a methoxy, a thiomethyl or a nitro or two of them can form a ring, in particular a phenyl in the case of the triazoloquinolines or the triazoloisoquinolines; and the non-toxic acid addition salts. These products are useful as drugs and possess analgesic properties, acting especially on the central nervous system as minor tranquilizers.
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