Abstract
Two kinds of [3 + 2] cycloaddition intermediates generated from the three-component reactions of 2-bromobenzaldehydes and maleimides with amino esters or amino acids were used for a one-pot N-allylation and intramolecular Heck reactions to form pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines. The multicomponent reaction was combined with one-pot reactions to make a synthetic method with good pot, atom and step economy. MeCN was used as a preferable green solvent for the reactions.
Highlights
Pyrrolo[2,1-a]isoquinoline and hexahydropyrrolo[2,1a]isoquinoline are privileged heterocyclic rings existing in many natural products and synthetic compounds possessing antitumor, antibacterial, antiviral, antioxidizing, and other biological activities (Figure 1) [1,2]
Adduct 5a generated from [3 + 2] cycloaddition was used as a model compound to develop the reaction conditions for the onepot N-allylation and intramolecular Heck reactions (Table 1)
We have developed an efficient method through a three-component [3 + 2] cycloaddition followed by a one-pot N-allylation and an intramolecular Heck reaction for the synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines
Summary
Pyrrolo[2,1-a]isoquinoline and hexahydropyrrolo[2,1a]isoquinoline are privileged heterocyclic rings existing in many natural products and synthetic compounds possessing antitumor, antibacterial, antiviral, antioxidizing, and other biological activities (Figure 1) [1,2]. We like to report in this paper our effort on the synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines via sequential 1,3-dipolar cycloaddition, N-allylation, and intramolecular Heck cyclization reactions [50,51,52,53,54] (Scheme 2, K).
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