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Synthetic study demonstrates catalyst-free multicomponent reactions of cyclic tertiary amines and aryl halides with sodium sulfide, highlighting a streamlined route to the analgesic ruzadolane.
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.
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Zhu et al. (2017) studied this question.
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