Allylic Amination andN-Arylation-Based Domino Reactions Providing Rapid Three-Component Strategies to Fused Pyrroles with Different Substituted Patterns

Abstract

New three-component domino reaction providing divergent approaches to multi-functionalized fused pyrroles with different substituted patterns have been established (40 examples). The direct C(sp3)–N bond formation was achieved through intermolecular allylic amination in a one-pot operation; and N-arylation of amines was realized by varying N-amino acid enaminones. The reaction is easy to perform simply by mixing three common reactants in acetic acid under microwave heating. The reaction proceeds at fast rates and can be finished within 30 min, which makes workup convenient to give good chemical yields.

C–N bond forming cross-coupling reactions: an overview

“…A three-component domino reaction has been developed by Tu, Li and co-workers 48 Recently, the synthesis of N-substituted phenoxazines 127 and related aza-analogs has been reported by Bolm and Thome 49 starting from N-acetylated aryloxy anilides 128 by transition metal-free, base catalyzed cyclization in the presence of DMEDA (10 mol%) and K 2 CO 3 in toluene (Scheme 36). Various substrates worked well with this catalytic system.…”

Recent advances in the synthesis of pyrroles via multicomponent reactions using arylglyoxals

“…This method is based on the microwave-promoted reaction between various N-substituted enaminones 63 and arylamines 8 with arylglyoxals 4 in the presence of acetic acid (Scheme 25). 97 Scheme 25. Jiang's synthesis of polyfunctionalized fused pyrroles.…”

“…Jiang's synthesis of polyfunctionalized fused pyrroles. 97 Recently, Jiang's group has reported a series of three-component reaction between arylglyoxals 4, enamonones 63, and an arylamine 8 to form 3-arylaminoindole derivatives 68 (Scheme 26). 98 Scheme 26.…”

Efficient Synthesis of Terpyrrole Derivatives by a Pseudo-Five-Component Reaction between Pyrrole, β-Enaminocarbonyls and Arylglyoxals

“…17 Multi-component reactions of arylglyoxals and enaminones in the presence of different nucleophiles have been recently utilised for synthesis of poly-functionalised pyrroles. [18][19][20] In continuation of our previous studies on the application of arylglyoxal multi-component reactions for synthesis of five-membered heterocyclic compounds, 21 here we report a facile and one-pot method for synthesis of some terpyrrole derivatives by reaction between pyrrole, arylglyoxals and enaminocarbonyl derivatives in the presence of ferric tribromide as catalyst.…”