Recent Development on the Ring Transformation Reactions: Synthesis of Functionalized Benzenes, N-Heterocycles and Fused Ring Systems

Singh, Fateh V.; Kole, Priyanka B.

doi:10.3987/rev-20-sr(k)8

Cited by 6 publications

(1 citation statement)

References 99 publications

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“…The fascinating chemistry of 2 H -pyran-2-ones has sparked much attention over the past several decades since they serve as excellent starting materials for the synthesis of a wide range of molecular structures. Recently, we have demonstrated the synthesis of 2-tetralones, 20 diarylmethanes, 21 m -terphenyls, 22 tetrahydroisoquinolines, 23 allylbenzenes, 24 and prenylarenes. 25 In order to study the wider scope of lactone chemistry, we aimed to explore ( E )-styryl acetate 2 as the possible carbanion nucleophile for the ring transformation reaction of 2 H -pyran-2-ones 1 .…”

Section: Table 1 Optimization Of Base For the Reaction ...mentioning

confidence: 99%

Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology

Krishnan

Singh

2022

Synthesis

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The function of styryl acetate as a carbanion nucleophile source has been explored in the ring transformation reaction of 2H-pyranones. The ultrasound assisted carbanion induced ring transformation of 4-amino-6-aryl-3-cyano-2H-pyran-2-ones using (E)-styryl acetate in the presence of KOH and DMF at room temperature is presented as an alternative strategy for the synthesis of functionalized 1,2-teraryls in high yields. This metal-free methodology provides easy access to a series of 1,2-teraryls and features broad functional group tolerance and mild reaction condition. Single crystal X-ray diffraction analysis of 4-(piperidin-1-yl)-6-(thiophen-2-yl)-[1,1'-biphenyl]-3-carbonitrile indicated that the crystal belongs to monoclinic system with a P21 space group having twisted aryl rings.

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Section: Table 1 Optimization Of Base For the Reaction ...mentioning

confidence: 99%

Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology

Krishnan

Singh

2022

Synthesis

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Ring Transformation of Cyclopropenes to Benzo‐Fused Five‐Membered Oxa‐ and Aza‐Heterocycles via a Formal [4+1] Cyclization

Gu,

Lin,

Peng

et al. 2024

Advanced Science

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In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting the distinctive properties of cyclopropenes, this study introduces an innovative approach for the synthesis of benzo‐fused five‐membered oxa‐ and aza‐heterocycles through a formal [4+1] cyclization and subsequent acid‐catalyzed intramolecular O‐ to N‐ rearrangement. These transformations exhibit mild reaction conditions and a wide substrate scope. The applications in the late‐stage modification of complex molecules and in the synthesis of a potential PD‐L1 gene down‐regulator, make this method highly appealing in related fields. Combined experimental mechanistic studies and DFT calculations demonstrate Rh(III)‐mediated sequential C─H coupling/π‐allylation/dynamically favorable O‐attack route.

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The literature of heterocyclic chemistry, Part XXI, 2021

Belen’kii,

Gazieva,

Evdokimenkova

et al. 2024

Advances in Heterocyclic Chemistry

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Recent Development on the Ring Transformation Reactions: Synthesis of Functionalized Benzenes, N-Heterocycles and Fused Ring Systems

Cited by 6 publications

References 99 publications

Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology

Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology

Ring Transformation of Cyclopropenes to Benzo‐Fused Five‐Membered Oxa‐ and Aza‐Heterocycles via a Formal [4+1] Cyclization

The literature of heterocyclic chemistry, Part XXI, 2021

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