Transition‐Metal‐Free Regioselective Construction of Diverse 3‐Carbonyl Functionalized 4‐Pyrones <i>via</i> Thermal Wolff‐Rearrangement of Diazodicarbonyls

Park, Ga Eul; Maezono, Shizuka Mei Bautista; Ha, Ji Hyeon; Shim, Jae‐Jin; Kim, Sung Hong; Lee, Yong Rok

doi:10.1002/adsc.201800874

Cited by 11 publications

(2 citation statements)

References 65 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N , N -Dimethyl enaminones, as attractive building blocks, have drawn much attention for their growing applications in constructing diverse heterocyclic motifs. 11 Recently, Zhu's group demonstrated an elegant work about Rh( iii )-catalyzed [4+2] annulation of enaminones with either alkynes or α-diazo-β-ketoesters to synthesize naphthalenes (Scheme 1a). 12 Afterwards, Yan's group reported a Rh( iii )-catalyzed C–H activation and annulation between enaminones and vinylene carbonate to construct 1-hydroxy-2-naphthaldehydes.…”

mentioning

confidence: 99%

Rh(iii)-catalyzed C–H/C–C bond annulation of enaminones with iodonium ylides to form isocoumarins

et al. 2022

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Rh(iii)-catalyzed C–H/C–C bond annulation of enaminones with iodonium ylides to form isocoumarins

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Subsequently, Lee developed an efficient protocol for the synthesis of 2,3,5-trisubstituted 4-pyrones using a unique thermal cascade reaction of N,N-dimethyl enaminones and diazodicarbonyls (Scheme 48). 51 Cyclic or acyclic diazodicarbonyl compounds could be employed in this transformation to afford diverse 3-carbonyl-functionalized 4-pyrone derivatives. Firstly, the diazodicarbonyls participated in a thermal Wolff rearrangement to provide the corresponding ketene 38 via carbene 37.…”

Section: Review Synthesismentioning

confidence: 99%

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Huang

2020

Synthesis

View full text Add to dashboard Cite

Enaminones are gaining increasing interest because of their unique properties and their importance in organic synthesis as versatile building blocks. N,N-Dimethyl enaminones offer a better leaving group (a dimethylamine group) than other enaminones, and allow further elaboration via a range of facile chemical transformations. Over the past five years, there have been an increasing number of reports describing the synthetic applications of N,N-dimethyl enaminones. This review provides a comprehensive overview on the synthetic applications of N,N-dimethyl enaminones that have been reported since 2016.1 Introduction2 Direct C(sp2)–H α-Functionalization2.1 Synthesis of α-Sulfenylated N,N-Dimethyl Enaminones2.2 Synthesis of α-Thiocyanated N,N-Dimethyl Enaminones2.3 Synthesis of α-Acyloxylated N,N-Dimethyl Enaminones3 Functionalization Reactions via C=C Double Bond Cleavage3.1 Synthesis of Functionalized Methyl Ketones3.2 Synthesis of α-Ketoamides, α-Ketoesters and 1,2-Diketones3.3 Synthesis of N-Sulfonyl Amidines4 Construction of All-Carbon Aromatic Scaffolds4.1 Synthesis of Benzaldehydes4.2 Synthesis of the Naphthalenes5 Construction of Heterocyclic Scaffolds5.1 Synthesis of Five-Membered Heterocycles5.2 Synthesis of Six-Membered Heterocycles5.3 Synthesis of Quinolines 5.4 Synthesis of Functionalized Chromones5.5 Synthesis of Other Fused Polycyclic Heterocycles6 Conclusions and Perspectives

show abstract

Rhodium(III)‐Catalyzed Regioselective C−H Activation/Annulation for the Diverse Pyrazole‐Core Substituted Furans

Cai

Thombal

et al. 2019

Adv Synth Catal

Self Cite

View full text Add to dashboard Cite

A novel and facile regioselective synthetic method for polyfunctionalized furans involving rhodium (III)-catalyzed pyrazole-or indazole-directed dual CÀ H functionalization with diazodicarbonyls has been developed. This strategy provides rapid access to diverse tetrasubstituted furans bearing various pyrazoles or indazoles. This unprecedented one-pot protocol proceeds via cascade CÀ H activation, metal-carbene formation, migratory insertion, intramolecular cyclization, and deprotonation. Ethyl 4-((1H-pyrazol-1-yl)methyl)-2-(4-methoxyphenyl)-5phenylfuran-3-carboxylate (3 j). Yellow liquid; yield -69 mg; HRMS (EI + ): m/z: calcd for C 24 H 22 N 2 O 4 : 402.1580, Found: 402.1581.Ethyl 4-((1H-pyrazol-1-yl)methyl)-2-(4-nitrophenyl)-5-phenylfuran-3-carboxylate (3 k). Yellow solid; yield -69 mg; 83%; mp 99-100°C; IR (KBr): v˜= H NMR (600 MHz, CDCl 3 ): δ = 8.27 (d, J = 9.6 Hz, 2H), 8.06 (d, J = 9.6 Hz, 2H), 7.78 (d, J = 7.2 Hz, 2H), 7.57 (d, J = 1.2 Hz, 1H),

show abstract

Transition‐Metal‐Free Regioselective Construction of Diverse 3‐Carbonyl Functionalized 4‐Pyrones via Thermal Wolff‐Rearrangement of Diazodicarbonyls

Cited by 11 publications

References 65 publications

Rh(iii)-catalyzed C–H/C–C bond annulation of enaminones with iodonium ylides to form isocoumarins

Rh(iii)-catalyzed C–H/C–C bond annulation of enaminones with iodonium ylides to form isocoumarins

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Rhodium(III)‐Catalyzed Regioselective C−H Activation/Annulation for the Diverse Pyrazole‐Core Substituted Furans

Contact Info

Product

Resources

About