Abstract
A novel isocyanide-based multicomponent synthesis of alkyl aryl(indol-3-yl)acetimidates has been established. Starting from aryl(indol-3-yl)methylium tetrafluoroborates, aromatic isocyanides and alcohols, the imidates were obtained in moderate to very good yields. Consecutive four-component synthesis of the above mentioned imidates from N-alkylindoles, aromatic aldehydes, aromatic isocyanides and alcohols was also proposed. In addition, it was shown that in the presence of water, aryl(indol-3-yl)methylium tetrafluoroborates reacted with isocyanides to furnish aryl(indol-3-yl)acetamides.
Highlights
Multicomponent reactions (MCRs) serve as a powerful and widely used instrument in organic synthesis (Shiri, 2012; Müller, 2014; Zarganes-Tzitzikas et al, 2015; Zhu et al, 2015; Levi and Müller, 2016)
A special place among them is occupied by transformations with the participation of isocyanides, unique reagents where nucleophiles and electrophiles attack the same atom
Starting salts 1a-f were obtained by alkylation of the corresponding indoles followed by reaction of N-benzylindoles 2a-c with aromatic aldehydes 3a-c under conditions similar to a previously published procedure (Figure 2) (Follet et al, 2015)
Summary
Multicomponent reactions (MCRs) serve as a powerful and widely used instrument in organic synthesis (Shiri, 2012; Müller, 2014; Zarganes-Tzitzikas et al, 2015; Zhu et al, 2015; Levi and Müller, 2016). Reactions of isocyanides with α,β-unsaturated imines or the corresponding iminium salts with the possibility of 1,4-addition are still rare (Marchand et al, 1999; Fontaine et al, 2009; Shimizu et al, 2009). Such imine and iminium salts were used in a formal [4+1] cycloaddition reaction with the formation of a pyrrole ring (Marchand et al, 1999; Fontaine et al, 2009; Kaur et al, 2016). The interaction of isocyanides with α,β-unsaturated imines could well-evolve into a novel multicomponent reaction
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