Exploitation of donor–acceptor cyclopropanes and <i>N</i>-sulfonyl 1-azadienes towards the synthesis of spiro-cyclopentane benzofuran derivatives

Verma, Kamal; Taily, Irshad Maajid; Banerjee, Prabal

doi:10.1039/c9ob01369e

Cited by 20 publications

(4 citation statements)

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“… 10 However, only a few catalytic asymmetric syntheses of spiro-cyclopentanone benzofurans are known. 11 Thus, an efficient route for the preparation of such a motif in enantioselective fashion is highly desirable. We speculated that such a motif can be generated by reacting only the C C of aurone-derived α,β-unsaturated imine.…”

Section: Introductionmentioning

confidence: 99%

Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

Khuntia,

Mahapatra,

Roy

et al. 2023

Chem. Sci.

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Section: Introductionmentioning

confidence: 99%

Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

Khuntia,

Mahapatra,

Roy

et al. 2023

Chem. Sci.

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“…In 2019, Banerjee and co-workers reported a different reactivity in the presence of an oxygen atom leading to a (3+2) cycloaddition product, namely the spirocyclopentane benzofuran derivative. 26…”

Section: Synthesis Of Nitrogen Heterocyclesmentioning

confidence: 99%

Synthesis of Heterocycles from Donor-Acceptor Cyclopropanes: A Five-Year Recap

Deepthi¹,

Meenakshy²,

Mohan³

2023

Synthesis

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The utility of donor-acceptor cyclopropanes (DACs) for the construction of heterocycles is discussed here. In addition to (3+2), (3+3) and (4+3) cycloaddition pathways, nucleophilic ring-opening reactions, intramolecular transformations and cycloisomerizations in presence of suitable catalysts pave way for the generation of heterocycles from DACs. Mild reactions conditions employed and the variety of starting materials that can be used as reaction partners makes the DAC route for heterocycle synthesis attractive. The literature from 2018-2023 is categorized as below. 1 Introduction 2 Synthesis of Nitrogen heterocycles 2.1 By annulations with anthranils and azadienes 2.2 By nucleophilic attack of anilines and hydrazones 2.3 By reaction with ureas and thioureas 2.4 By annulation reactions using azomethine imine 2.5 By reaction with other N-heterocycles 2.6 By other transformations 3 Synthesis of Oxygen heterocycles 3.1 By intramolecular transformations 3.2 By intermolecular reactions 4 Synthesis of Sulphur/Selenium heterocycles 4.1 By reaction with thiocarbonyl substrates 4.2 By reaction with thio/selenocyanates and thiosulfonate salts 5 Synthesis of N-S/O heterocycles 6 Conclusions

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“…However, there is a paucity of examples demonstrating the formation of seven-membered rings through the utilization of DACs as 1,3-dipoles. The challenge lies in the competitive 1,2-addition with DACs to form (3 + 2) cycloaddition products . The first study on (4 + 3) addition with DACs was reported by Ivanova and co-workers in 2008, which disclosed iso-benzofuran as a cyclic diene participating in the cycloaddition reaction with DACs .…”

Section: Introductionmentioning

confidence: 99%

Yb(OTf)₃-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with Donor–Acceptor Cyclopropanes

Jiang,

Ma,

Wang

et al. 2023

J. Org. Chem.

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A Yb(OTf)3-catalyzed formal (4 + 3) cycloaddition reaction of donor–acceptor cyclopropanes with 3-benzylideneindoline-2-thiones as sulfur-containing 4π components has been successfully achieved. A series of functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized with good yields and moderate to good diastereoselectivity. The reaction described herein represented the inaugural (4 + 3) cycloaddition of 3-benzylideneindoline-2-thiones.

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Exploitation of donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes towards the synthesis of spiro-cyclopentane benzofuran derivatives

Abstract: An efficient method for the synthesis of spiro-cyclopentane benzofuran derivatives via a MgI2-catalyzed formal [3 + 2] cycloaddition reaction between donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes in good yield has been developed.

Cited by 20 publications

References 41 publications

Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

Synthesis of Heterocycles from Donor-Acceptor Cyclopropanes: A Five-Year Recap

Yb(OTf)₃-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with Donor–Acceptor Cyclopropanes

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Exploitation of donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes towards the synthesis of spiro-cyclopentane benzofuran derivatives

Abstract: An efficient method for the synthesis of spiro-cyclopentane benzofuran derivatives via a MgI2-catalyzed formal [3 + 2] cycloaddition reaction between donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes in good yield has been developed.

Cited by 20 publications

References 41 publications

Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis

Synthesis of Heterocycles from Donor-Acceptor Cyclopropanes: A Five-Year Recap

Yb(OTf)3-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with Donor–Acceptor Cyclopropanes

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Yb(OTf)₃-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with Donor–Acceptor Cyclopropanes