Synthesis of 1,4-Dihydroquinolines and 4<i>H</i>-Chromenes via Organocatalytic Domino Aza/Oxa-Michael/1,6-Addition Reactions of <i>para</i>-Quinone Methides and Ynals

Wang, Junwei; Rong, Quanjin; Zhao, Lei; Pan, Xiang; Zhao, Lin; Zhao, Kun; Hu, Lihong

doi:10.1021/acs.joc.0c01315

Cited by 34 publications

(9 citation statements)

References 67 publications

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“…In 2020, Hu and co‐workers reported a highly efficient synthetic method to 4‐aryl‐1,4‐dihydroquinolines through morpholine catalyzed aza‐Michael/1,6‐conjugate addition cascade reactions of ortho ‐tosylaminophenyl‐ p ‐QMs with ynals [56] . In addition, this strategy can also be extended to ortho ‐hydroxyphenyl‐substituted p ‐QMs for the synthesis of 4‐aryl‐4 H ‐chromene derivatives.…”

Section: Catalytic Asymmetric Aza‐michael Addition Triggered Cascade Reactionsmentioning

confidence: 99%

Recent Advances in Catalytic Asymmetric Aza‐Michael Addition Triggered Cascade Reactions

Song

2021

Adv Synth Catal

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As an important branch of the Michael addition reaction, the aza‐Michael addition cascade reaction has been developed rapidly in recent years. This is because the reaction serves as an important method for effectively constructing functionalized C−N bonds, which can be widely used in the synthesis of chiral drugs and their intermediates and natural products. Given the importance of this topic, this review highlights the recent developments of aza‐Michael addition triggered cascade reactions in asymmetric synthesis, including aza‐Michael/Michael, aza‐Michael/Aldol, aza‐Michael/Henry, aza‐Michael/hemiacetal, aza‐Michael/Mannich, aza‐Michael/alkylation, aza‐Michael/cyclization, aza‐Michael/ring‐opening, aza‐Michael‐IED/HAD, aza‐Michael/INCR, and aza‐Michael/1,6‐conjugate addition reactions. In this paper, the reaction mechanism and derivatization experiments of different reactions are timely introduced to provide a more comprehensive theoretical basis for subsequent studies.

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Section: Catalytic Asymmetric Aza‐michael Addition Triggered Cascade Reactionsmentioning

confidence: 99%

Recent Advances in Catalytic Asymmetric Aza‐Michael Addition Triggered Cascade Reactions

Song

2021

Adv Synth Catal

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“…[77] Later, the same group also reported an organocatalytic method to the synthesis of 1,4-dihydroquinolines (186) through an aza-Michael type addition reaction of 172 with ynals (185) followed by intramolecular 1,6-addition/ cyclization (Scheme 48). [78] Samanta's group disclosed an interesting 1,4-diazabicyclo [2.2.2]octane (DABCO)-mediated protocol for the synthesis of substituted pyridines (189), from vinyl-substituted p-QMs (187) and cyclic sulfamidate-imines (188) [Scheme 49]. [79] The authors proposed that the base (DABCO) abstracts a Scheme 45.…”

Section: Synthesis Of Dihydro-/tetrahydro-quinolines and Pyridine-based N-heterocyclesmentioning

confidence: 99%

Construction of Oxygen‐ and Nitrogen‐based Heterocycles from p‐Quinone Methides

Singh

Pandey

Pankhade

et al. 2021

The Chemical Record

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In the last few years, there has been an explosive growth in the area of para-quinone methide (p-QM) chemistry. This boom is actually due to the unique reactivity pattern of p-QMs, and also their remarkable synthetic applications. In fact, p-QMs serve as synthons for unsymmetrical diaryl-and triarylmethanes, and also for the construction of diverse range of carbocycles and heterocycles. In the last few years, a wide range of structurally complex heterocyclic frameworks could be accessed through the synthetic transformations of structurally modified stable p-QMs. Therefore, the main focus of this review article is to cover the recent advancements in the transition-metal, Lewis acid and base-catalyzed/mediated synthetic transformations of the stable p-quinone methides (p-QMs) to oxygen-and nitrogen-containing heterocycles.

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“…Due to the unique bisvinylogous enone structure, p -quinone methides ( p -QMs) are considered as electron-deficient alkenes, which have been widely employed in organic synthesis, especially in the 1,6-conjugated addition and intermolecular cyclization transformation. − Fan et al established a novel and efficient catalytic asymmetric 1,6-conjugate addition/aromatization of p -QMs with malonates, oxindoles, and glycine derivatives via the catalysis of small organic chiral amines . In 2014, Jørgensen et al disclosed a chiral secondary amine catalyzed asymmetric α-alkylation of aldehydes through the 1,6-conjugated addition of enamines with p -QMs, where a series of α-diarylmethyl-substituted aldehydes with two contiguous stereocenters was synthesized with good yields and excellent enantioselectivity .…”

Section: Introductionmentioning

confidence: 99%

Metal-Free, Acid/Phosphine-Induced Regioselective Thiolation of p-Quinone Methides with Sodium Aryl/Alkyl Sulfinates

Xiong

Tang

et al. 2021

J. Org. Chem.

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A simple and efficient method for the regioselective thiolation of p-quinone methides with sodium aryl/alkyl sulfinates has been established using an acid/phosphine-induced radical route under transition-metal-free conditions. A broad range of sodium aryl/alkyl sulfinates and p-quinone methides (p-QMs) are compatible for the reaction, giving the expected products with good to excellent yields. Control experiments were also performed to gain insights into the generation mechanism of thiyl radicals and hydrogen-atom transfer process. This protocol provides a safe and feasible way for the formation of carbon−sulfur bonds.

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Synthesis of 1,4-Dihydroquinolines and 4H-Chromenes via Organocatalytic Domino Aza/Oxa-Michael/1,6-Addition Reactions of para-Quinone Methides and Ynals

Cited by 34 publications

References 67 publications

Recent Advances in Catalytic Asymmetric Aza‐Michael Addition Triggered Cascade Reactions

Recent Advances in Catalytic Asymmetric Aza‐Michael Addition Triggered Cascade Reactions

Construction of Oxygen‐ and Nitrogen‐based Heterocycles from p‐Quinone Methides

Metal-Free, Acid/Phosphine-Induced Regioselective Thiolation of p-Quinone Methides with Sodium Aryl/Alkyl Sulfinates

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