Catalyst-free direct regiospecific multicomponent synthesis of C3-functionalized pyrroles

Pawar, Amol Prakash; Yadav, Jyothi; Dolas, Atul Jankiram; Iype, Eldhose; Rangan, Krishnan; Kumar, Indresh

doi:10.1039/d2ob00961g

Cited by 6 publications

(3 citation statements)

References 124 publications

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“…[32] At first, the ). [33] The mechanism of this synthetic protocol follows the Paal-Knorr reaction in which an enamine intermediate, in situ generated from succinaldehyde and a primary amine 3, was trapped with activated carbonyls before the Paal-Knorr reaction. Under the optimized conditions, a series of C 3functionalized pyrrole scaffolds 116 were synthesized in moderate to good yields.…”

Section: Synthesis Of Pyrroles and Pyrrolidinesmentioning

confidence: 99%

“…developed a regiospecific MCR for the synthesis of C 3 ‐functionalized pyrrole 116 scaffolds from succinaldehyde, amines 3 and α‐acylcarbonyls 115 in CH 2 Cl 2 /EtOH (1 : 1) under mild conditions (Scheme 17). [33] The mechanism of this synthetic protocol follows the Paal–Knorr reaction in which an enamine intermediate, in situ generated from succinaldehyde and a primary amine 3 , was trapped with activated carbonyls before the Paal–Knorr reaction. Under the optimized conditions, a series of C 3 ‐functionalized pyrrole scaffolds 116 were synthesized in moderate to good yields.…”

Section: Five‐membered Heterocyclic Compoundsmentioning

confidence: 99%

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Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, the use of transition metal catalysts or additives in MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest in transition metal‐free MCRs for the synthesis of N‐heterocyclic compounds. This review provides a comprehensive and concise overview of the recent advancements in transition metal‐free MCRs for the synthesis of valuable N‐heterocycles over the past five years. The review is systematically organized, categorizing the discussed MCRs based on the size of the heterocyclic ring and the number of nitrogen atoms. Only MCRs that result in the formation of heterocyclic rings containing at least one nitrogen atom are included, while the derivatization of N‐heterocycles using transition metal‐free MCRs falls outside the scope of this review. By highlighting the recent developments in this field, this review aims to showcase the potential and significance of transition metal‐free MCRs as sustainable and efficient strategies for accessing N‐heterocyclic compounds. The elimination of transition metals not only simplifies the reaction conditions but also contributes to greener and more environmentally friendly synthetic approaches. This review serves as a valuable resource for researchers interested in the design and application of transition metal‐free MCRs in the synthesis of nitrogen‐containing heterocycles.

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Section: Synthesis Of Pyrroles and Pyrrolidinesmentioning

confidence: 99%

Section: Five‐membered Heterocyclic Compoundsmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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“…Succinaldehyde has recently been exploited extensively in metal-free cascade reactions, in addition to its early utilization in tropone synthesis and the Paal–Knorr reaction, along with other one-pot transformations . Because of our continued research interest in utilizing succinaldehyde for metal-free transformations, we recently developed direct methods for accessing C3-substituted pyrrole using mild Lewis acid and catalyst-free conditions . The focus of the study presented here is to exploit the potential of the chiral amine-catalyzed aldol reaction of succinaldehyde with acceptor carbonyls before it undergoes the Paal–Knorr reaction with a primary amine to afford substitution with chirality at position C3 of pyrrole.…”

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Enantioselective Direct Synthesis of C3-Hydroxyalkylated Pyrrole via an Amine-Catalyzed Aldol/Paal–Knorr Reaction Sequence

et al. 2022

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Creating functionality with chirality at position C3 of pyrrole is challenging. An operationally simple organocatalytic method has been developed to generate functionality with a chiral tertiary/quaternary stereocenter at position C3 of pyrrole. The process proceeds through an amine-catalyzed direct aldol reaction of succinaldehyde with various acceptor carbonyls, followed by a Paal–Knorr reaction with a primary amine in the same pot. A series of chiral C3-hydroxyalkylated N-alkyl/Ar/H-pyrroles have been synthesized for the first time with good to high yields and excellent enantioselectivity.

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Elevating pyrrole derivative synthesis: a three-component revolution

Kumar S.,

Servesh,

Chundattu

et al. 2024

Mol Divers

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Catalyst-free direct regiospecific multicomponent synthesis of C3-functionalized pyrroles

Abstract: An operationally simple catalyst-free protocol for the direct regiospecific synthesis of β-(C3)-substituted pyrrole has been developed. The enamine-intermediate, in situ generated from succinaldehyde and a primary amine, was trapped with...

Cited by 6 publications

References 124 publications

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Enantioselective Direct Synthesis of C3-Hydroxyalkylated Pyrrole via an Amine-Catalyzed Aldol/Paal–Knorr Reaction Sequence

Elevating pyrrole derivative synthesis: a three-component revolution

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