An eco-friendly three-component regio- and stereoselective synthesis of highly functionalized dihydroindeno[1,2-b]pyrroles under grinding

Multicomponent mechanochemical synthesis

“…These structurally interesting compounds were synthesized as single diastereomers by Perumal and coworkers by simply grinding for short times equimolecular amounts of ( E )-3-(dimethylamino)-1-arylprop-2-en-1-ones 29 with anilines and ninhydrin 30 in the presence of a small amount of acetic acid, and were isolated in pure state without the need for chromatographic purification. 35 …”

Domino Reactions Based on Combinatorial Bond Transformations in Electron-Deficient Tertiary Enamines

“…Also by means of the primary amine transamination, Perumal et al reported the synthesis of fused dihydropyrroles 19 via the three‐component reactions of enaminones 1 , primary amines 2 , and ninhydrin 18 . The main steps during the formation of fused products were the transamination and the formal double nucleophilic addition of both the NH and α‐carbon in 6 to ninhydrin (Scheme ) 16. Moreover, the group recently reported another three‐component reaction involving the transamination of enaminones 1 and primary amines 2 for the one‐pot synthesis of functionalized chromones 21 in the presence of 3‐formylchromone 20 .…”

“…The main steps during the formation of fused products were the transamination and the formal double nucleophilic addition of both the NH and a-carbon in 6 to ninhydrin (Scheme 7). [16] Moreover, the group recently reported another three-component reaction involving the transamination of enaminones 1 and primary amines 2 for the one-pot synthesis of functionalized chromones 21 in the presence of 3formylchromone 20. As outlined in Scheme 8, it was proposed that the formation of secondary enaminones 6 and a subsequent Baylis-Hillman reaction with 20 provided adducts 22.…”

Efficient and Uncatalyzed Synthesis of Highly Functionalized New Symmetrical Indeno[1,2‐b]pyrroles via a One‐Pot Four‐Component Reaction

“…Perumal et al . in 2014 demonstrated simple three‐component domino reactions of ( E )‐3‐(dimethylamino)‐1‐arylprop‐2‐en‐1‐one derivatives with anilines and ninhydrin in an equimolar ratio after grinding in the presence of HOAc to make highly substituted dihydroindeno[1,2‐ b ]pyrrole derivatives with regio‐ and stereoselectively in satisfactory yields . Noticeably, a very efficient method for the formation of indeno[1,2‐ b ]pyrrole derivatives containing bistriazole core from hydrazonoyl chlorides and oxaaza[3.3.…”