Mechanochemical N-alkylation of imides

Abstract

The mechanochemical N-alkylation of imide derivatives was studied. Reactions under solvent-free conditions in a ball mill gave good yields and could be put in place of the classical solution conditions. The method is general and can be applied to various imides and alkyl halides. Phthalimides prepared under ball milling conditions were used in a mechanochemical Gabriel synthesis of amines by their reaction with 1,2-diaminoethane.

Consecutive Utilization of Mechanochemical and Microwave Methods for the Synthesis of Boc‐2‐amino‐quinazolin‐4(3H)‐ones and DFT Study of Mechanism 6π‐Diazaelectrocyclization Process

“…For instance, two consecutive MW steps were employed for synthesis of acetoacetamido esters, [9] also three, [10] four [11,12] and as many as six MW steps [13] were utilized in synthesis of organic compounds. Multistep mechanochemical reactions were also developed, employing two, [14,15] three, [16] four [17] and five consecutive synthetic steps. [18] In general, combination of two sustainable synthetic methods could be carried out in two ways: by tandem use of two methods or their consecutive employment.…”

Complementarity of solution and solid state mechanochemical reaction conditions demonstrated by 1,2-debromination of tricyclic imides

“…One of the emerging synthetic methods is mechanochemistry [4][5][6][7], a greener alternative to carry out synthesis which complements heating, irradiation and electrochemistry as methods of chemical activation [8]. Based upon our experience in applications of this method to organic synthesis [9][10][11][12], we recognized its potential for the adjustment of conditions in zinc-mediated debromination reactions.…”

Mechanochemical Nucleophilic Substitution of Alcohols via Isouronium Intermediates

“…16 As a consequence, almost 80% of heteroatom alkylation and arylation reactions used in the synthesis of drug candidates involve the formation of C-N bonds. 17 In addition to the mainstream developments like amide synthesis, [18][19][20][21][22][23] the state-of-the-art mechanochemical synthetic toolbox offers several opportunities to construct C-N bonds 24 in amines via alkylation [25][26][27] and arylation [28][29][30] with organic halides. However, the use of alcohols as ubiquitous starting materials remains nearly untapped.…”