One-pot C–N/C–C bond formation and oxidation of donor–acceptor cyclopropanes with tetrahydroisoquinolines: access to benzo-fused indolizines

Karjee, Pallab; Debnath, Bijoy; Mandal, Santu; Saha, Sharajit; Punniyamurthy, Tharmalingam

doi:10.1039/d4cc00810c

Chem. Commun.

2024

DOI: 10.1039/d4cc00810c

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One-pot C–N/C–C bond formation and oxidation of donor–acceptor cyclopropanes with tetrahydroisoquinolines: access to benzo-fused indolizines

Pallab Karjee,

Bijoy Debnath,

Santu Mandal

et al.

Abstract: One-pot C-N/C-C bond formation of donor-acceptor cyclopropanes (DACs) with tetrahydroisoquinolines (THIQs) has been achieved to furnish benzo-fused indolizines. These reactions involve a MgI2-catalyzed ring opening of DACs and oxidative annulation...

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Cited by 3 publications

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Recent Advances in the Development of Indolizine Scaffolds: Synthetic Methodology and Mechanistic Insights

Huang,

Li,

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryIndolizine is a nitrogen‐containing heterocycle with strong aromaticity, possessing a delocalized 10π‐electron system. Based on the indolizine scaffolds, numerous molecules with biological activity and organic functional materials have been synthesized. Since 2016, over 110 papers have been published on the synthesis of indolizine scaffolds, but the reviews on synthesizing indolizine scaffolds have been incomplete and not up‐to‐date. Herein, from the perspective of the structure of indolizine with the combination of pyrrole and pyridine ring, we focus on the construction of indolizine scaffolds through the diversity of starting substrates, including pyridine derivatives (N1‐substituted pyridinium salt derivatives, C2‐substituted pyridine derivatives, N1‐ and C2‐free substituted pyridine derivatives), pyrrole derivatives and unoriginal ring substrates. Furthermore, the corresponding reaction mechanisms of synthetic methodologies are also elaborated. Therefore, this review not only paves the way for indolizine synthesis but also provides insight into exploring new reaction modes for constructing nitrogen‐containing heterocycles. Key ScientistsIndolizine was discovered by Angeli in 1890 and first prepared by Scholtz in 1912 from α‐picoline and acetic anhydride. A general approach was developed by Chichibabin in 1927, that is of practical value for the preparation of 2‐alkyl‐ or 2‐arylindolizines. The Chichibabin reaction was the ring closure of quaternary pyridinium halides. At the begining of the 21st century, Basavaiah introduced a new dimension in the Baylis‐Hillman chemistry leading to a novel facile convenient methodology for synthesis of indolizine scaffolds in one‐pot operation. In 2010, Barluenga reported Cu(I)‐catalyzed regioselective [3+2] cyclization of unsubstituted pyridines toward alkenyldiazoacetates leading to functionalized indolizine derivatives, that was the first successful example of metal‐catalyzed cyclization of a π‐deficient heterocyclic system with alkenyldiazo compounds. In 2019 and 2022, Xi and Liu exploited the methods of non‐pyridine derivatives as starting materials to synthesize indolizines, respectively. In 2022, Guo developed an environmentally benign electrooxidative approach for constructing formyl‐ and acyl‐substituted indolizines.

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Recent Advances in the Development of Indolizine Scaffolds: Synthetic Methodology and Mechanistic Insights

Huang,

Li,

et al. 2024

Chin. J. Chem.

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Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes through Umpolung Reactivity of Organochlorophosphines: Phosphine Oxide-Functionalized Boron-Pendanted Compounds

Gopal,

Lamba,

Kushwaha

et al. 2024

Org. Lett.

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We present a novel set of frustrated Lewis pair (FLP) systems that exhibit a remarkable ability to promote the ring opening of donor−acceptor cyclopropanes (DACs). This FLP-promoted protocol offers umpolung reactivity of R 1 R 2 PCl/CN (R 1 , R 2 = aryl, alkyl) toward DACs via nucleophilic ring-opening reactions to provide phosphinated boron-pendanted diester compounds. This novel approach exhibits the dual role of BF 3 •OEt 2 as an activator and a reactant. The resulting compounds were found in both the keto and enol forms, with the majority being in the keto form, according to NMR analysis. The enol form was identified by single-crystal XRD analysis, and DFT calculations indicated that the keto form is more stable than the corresponding enol form.

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Manganese(iii) acetate in organic synthesis: a review of the past decade

Wang,

Zhang,

Zhou

et al. 2024

Org. Chem. Front.

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One-pot C–N/C–C bond formation and oxidation of donor–acceptor cyclopropanes with tetrahydroisoquinolines: access to benzo-fused indolizines

Abstract: One-pot C-N/C-C bond formation of donor-acceptor cyclopropanes (DACs) with tetrahydroisoquinolines (THIQs) has been achieved to furnish benzo-fused indolizines. These reactions involve a MgI2-catalyzed ring opening of DACs and oxidative annulation...

Cited by 3 publications

References 75 publications

Recent Advances in the Development of Indolizine Scaffolds: Synthetic Methodology and Mechanistic Insights

Recent Advances in the Development of Indolizine Scaffolds: Synthetic Methodology and Mechanistic Insights

Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes through Umpolung Reactivity of Organochlorophosphines: Phosphine Oxide-Functionalized Boron-Pendanted Compounds

Manganese(iii) acetate in organic synthesis: a review of the past decade

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