Co(III)-Catalyzed Enaminone-Directed C–H Amidation for Quinolone Synthesis

Shi, Pengfei; Wang, Lili; Chen, Kehao; Wang, Jie; Zhu, Jin

doi:10.1021/acs.orglett.7b00968

Cited by 91 publications

(38 citation statements)

References 60 publications

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“…The effect of the bases was subsequently investigated (entries 2-7). Na 2 CO 3 and Cs 2 CO 3 could provide the desired product in good yields (entries 2,3), while lower yields of 3 aa were obtained in the present of KHCO 3 , NaHCO 3 , and K 3 PO 4 (entries [4][5][6]. However, the target product was not detected and only a complex mixture was obtained when a strong base KO t Bu was involved in the reaction (entry 7).…”

Section: Resultsmentioning

confidence: 99%

“…4,162.4,155.1,152.0,140.2,136.1,135.8,134.1,132.8,129.2,128.9,128.6,128.3,127.6,127.3,126.8,125.4,125.1,124.6,124.3,122.7,121.0,117.5,116.5,52.7 .HRMS (EI) (d,J = 8.2 Hz,2H),1H),2H),3H),7.24 (d,J = 8.2 Hz, 2H), 7.08-7.03 (m, 2H), 6.99 (d, J = 7.1 Hz, 2H), 6.86 (t, J = 8.0 Hz, 2H), 5.26 (s, 2H); 13 C NMR (126 MHz, CDCl 3 ) δ 175.6, 162.8 (d,J = 251.7 Hz),151.7,146.1,143.1,140.7,135.8,133.0,132.3,131.0 (d,J = 8.4 Hz), 129.7 (d, J = 3.8 Hz), 129. 1, 127.8, 127.3, 126.7, 125.3, 124.4, 122.8, 117.3, 115.8 (d, 7,151.5,146.2,142.9,140.7,135.8,135.7,133.0,132.3,132.0,130.3,…”

Section: General Procedures For the Preparation Of 123-trisubstitutementioning

confidence: 99%

“…5, 122.8, 122.5, 117.3, 116.7 (d, J = 20.7 (d,J = 8.5 Hz,2H),1H),2H),7.27 (t,J = 7.2 Hz,2H),3H),.07 (m, 1H), 6.98 (d, J = 7.3 Hz, 2H), 6.95-6.89 (m, 1H), 6.71 (d, J = 4.8 Hz, 1H), 5.24 (d, J = 9.1 Hz, 2H); 13 C NMR (126 MHz, CDCl 3 ) δ 175. 4,148.3,146.0,143.5,140.7,136.2,133.5,132.8,131.9,129.1,128.0,127.8,127.2,127.0,126.8,126.7,125.3,124.3,123.0,122.7,117.3,52.8;HRMS (EI) 9, 152.5, 147.0, 144.4, 141.1, 135.5, 132.5, 132.1, 129.3, 128.0, 127.1, 126.3, 125.2, 123.9, 123.6, 122.3, 116.4, 7, 152.0, 146.2, 143.9, 140.9, 136.0, 132.6, 132.2, 129.1, 127.6, 127.0, 126.2, 125.2, 123.8, 122.6, 122.6, 116.6, 50.4, 14.5, 11.2 (d,J = 264.8 Hz),152.21,146.05,142.81,142.77,135.65,133.33,132.83 (d,J = 11.0 Hz),132.38,129.59,129.06,128.94,128.57,127.79,…”

Section: General Procedures For the Preparation Of 123-trisubstitutementioning

confidence: 99%

“…Besides, harsh reaction conditions and tedious purification steps are usually required in these procedures, and the cyclization step using sterically hindered 2-aryl β-keto esters gives 3aryl-4-quinolones in poor yields. Although the development of methods to generate 4-quinolones has been an active area of research for the past decades, [4,5] synthetic methods for the construction of 4-quinolone core bearing an aryl group at C3 position are extremely rare. In this regard, the direct C3 functionalization of the 4-quinolone core represents an attractive route to 3-substituted 4-quinolones.…”

Section: Introductionmentioning

confidence: 99%

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Base‐Promoted Michael Addition/Smiles Rearrangement/ N‐Arylation Cascade: One‐Step Synthesis of 1,2,3‐Trisubstituted 4‐Quinolones from Ynones and Sulfonamides

Liu

et al. 2019

Adv Synth Catal

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A general, practical, and environmentally friendly protocol to synthesize 1,2,3‐trisubstituted 4‐quinolones from readily available ynones and sulfonamides was developed. The construction of one C−C bond and two C−N bonds via cleavage of one N−S, one C−S, and one C−X (X=F, Cl, Br, O) bond is achieved under transition‐metal‐free conditions in one step. This transformation generates 1 equiv. of sulfur dioxide and 1 equiv. of hydrogen halide as the byproducts. The broad substrate scope and functional group tolerance are demonstrated by 52 examples of 1,2,3‐trisubstituted 4‐quinolones. A preliminary mechanistic study supports a sequential Michael addition/Smiles rearrangement/N‐arylation reaction pathway.

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Section: Resultsmentioning

confidence: 99%

Section: General Procedures For the Preparation Of 123-trisubstitutementioning

confidence: 99%

Section: General Procedures For the Preparation Of 123-trisubstitutementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Base‐Promoted Michael Addition/Smiles Rearrangement/ N‐Arylation Cascade: One‐Step Synthesis of 1,2,3‐Trisubstituted 4‐Quinolones from Ynones and Sulfonamides

Liu

et al. 2019

Adv Synth Catal

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“…As an application of the developed method, numbers of amidated products were converted to NH quinolone derivatives under acid mediated cyclization. Subsequently, another report on similar enaminone directed C−H bond amidation of arenes was disclosed by Zhu and co‐workers employing slightly modified conditions using Cp*CoI 2 CO as catalyzed and AgBF 4 as additive, in the absence of base (Scheme b) …”

Section: Construction Of C‐heteroatom Bondmentioning

confidence: 99%

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations

Ghorai¹,

Anbarasan²

2019

Asian J Org Chem

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Transition-metal-catalyzed CÀ H bond functionalization has emerged as a powerful tool in contemporary organic synthesis. In this aspect, precious metal-based high-valent catalysts have been extensively studied. In the past decade, earth-abundant high-valent Cp*Co(III)-catalysts have emerged as a promising alternative to the expensive transition metals, providing unique selectivity and reactivity. In this Minireview, we summarized important progresses in the area of Cp*Co (III)-catalyzed CÀ H bond functionalization until 2017.[a] Mr. . Alkylation of CÀ H bonds with activated alkene. Scheme 3. Alkylation of CÀ H bonds with activated alkene. Scheme 4. Alkylation of CÀ H bonds with maleimides.Scheme 5. Alkylation of CÀ H bonds of (hetero)arene with maleimide. Scheme 6. Alkylation of CÀ H bonds with unactivated alkenes. Scheme 7. Allylation of CÀ H bonds with allyl carbonates. . Allylation of CÀ H bonds with allyl acetate. Scheme 9. Allylation of CÀ H bonds of arenes with allyl carbonates. Scheme 10. Allylation of CÀ H bonds with allyl alcohol. Scheme 11. Cobalt catalyzed allylation using allyl alcohol. Scheme 12. Cobalt catalyzed allylation with activated allylating reagent. . Cobalt catalyzed selective addition of C2À H bond to C=N bond. Scheme 18. Cobalt catalyzed selective addition of CÀ H bond to isocyanate. Scheme 19. Cobalt(III)-catalyzed aryl and alkenyl CÀ H aminocarbonylation. Scheme 20. Cobalt catalyzed hydroarylation to ketenimines. Scheme 21. Cobalt catalyzed synthesis of pyrroloindolones. Scheme 22. Cobalt catalyzed alkenylation through hydroarylation to alkyne. Co(III)-catalyzed alkenylation. Scheme 24. Cobalt catalyzed alkenylation of heterocyclic moiety. Scheme 25. Cp*Co III -Catalyzed branch-selective hydroarylation of alkynes. Scheme 26. Cobalt catalyzed C(sp 3 )À H alkenylation. . Cobalt(III)-catalyzed amidation with dioxazolone. Scheme 40. Mechanism of cobalt catalyzed amidation with dioxazolone. Scheme 41. Cobalt(III)-catalyzed CÀ H bond amidation using dioxazolone.

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