N-aryl azacycloalkanes

A novel double alkylation of aniline derivatives by alkyl dihalides occurred in mildly basic aqueous media upon microwave irradiation and afforded a series of N-aryl azacycloalkanes (Scheme 22) [89]. 

This microwave-accelerated double alkylation reaction was applicable to a variety of aniline derivatives and dihalides, furnishing N-aryl azacycloalkanes in good to excellent yields [89]. The reaction was applicable to alkyl chlorides, bromides and iodides and was extended to include hydrazines [90]. This improved synthetic methodology provided a simple and straightforward one-pot approach to the synthesis of a variety of heterocycles such as substituted azetidines, pyrrolidines, piperidines, azepanes, N-substituted-2,3-dihydro-Iff-isoindoles, 4,5-dihydro-pyrazoles, pyrazolidines, and 1,2-dihydro-phthalazines [91]. The mild reaction conditions tolerated a variety of functional groups such as hydroxyls, carbonyls, and esters. 

Reactions in Aqueous Media-synthesis of N-aryl Azacycloalkanes... 

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