Synthesis of pyrrolocoumarins via Pd-catalyzed domino C–N coupling/hydroamination reactions

Ngo, Thang Ngoc; Akrawi, Omer A.; Dang, Tuan Thanh; Villinger, Alexander; Langer, Peter

doi:10.1016/j.tetlet.2014.11.007

Cited by 19 publications

(11 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(f) Pyrrolocoumarins have been synthesized by the amino-Claisen rearrangement of propargylaminocoumarins under reflux in N , N -dimethylaniline. 15 (g) Palladium-catalyzed hydroamination of 4-alkynyl-3-aminocoumarins 16` b c or reaction of 4-aminocoumarins with alkynes 16d resulted in substituted pyrolocoumarins.…”

Section: Table 1 Allylation Of 4-arylaminocoumarins ...mentioning

confidence: 99%

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins

et al. 2022

View full text Add to dashboard Cite

Abstract1-Aryl-2-methyl- or 3-methylchromeno[4,3-b]pyrrol-4(1H)-ones have been synthesized in excellent yields by the Pd-catalyzed intramolecular aza-Wacker-type cyclization of 3-allyl-4-arylaminocoumarins or C–H insertion/oxidative cyclization of N-allyl-N-aryl-4-aminocoumarins, respectively, in the presence of Cu(OAc)2 in acetic acid under heating. The starting allylcoumarins have been prepared by the allylation of 4-arylaminocoumarins with allyl bromide in CH3CN in the presence of Cs2CO3 at room temperature. Preliminary biological tests indicated interesting antioxidant activity and significant levels of inhibition of soybean lipoxygenase.

show abstract

Section: Table 1 Allylation Of 4-arylaminocoumarins ...mentioning

confidence: 99%

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins

et al. 2022

View full text Add to dashboard Cite

show abstract

“…The Sonogashira reaction was also used in relation to cyclic bromovinyl triflates (Scheme S16). 35 The triflate moiety was chemoselectively substituted with a catalytic amount of both Pd(MeCN) 2 Cl 2 and copper iodide. The isolated products were then used in a palladium-catalyzed domino C-N coupling/hydroamination reaction to afford T. Edlová et al…”

Section: Short Review Synthesis Scheme S13 Stille-heck and Heck-stillmentioning

confidence: 99%

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

Edlová¹,

Čubiňák²,

Tobrman³

2020

Synthesis

View full text Add to dashboard Cite

This short review summarizes the latest advances in the cross-coupling reactions of double and triple electrophilic templates bearing halogen atoms and an activated C–O bond. Reactions involving the formation of a C–C bond as part of di-, tri-, and tetrasubstituted double bond systems are highlighted.1 Introduction2 Cross-Coupling Reactions of Halovinyl Tosylates3 Cross-Coupling Reactions of Halovinyl Triflates4 Cross-Coupling Reactions of Halovinyl Phosphates5 Cross-Coupling Reactions of Halovinyl Esters6 Conclusion

show abstract

“…43 Thus, the reaction of 3-bromo-4-ethynyl-coumarin derivatives 39 with amines 29, performed using Pd(OAc) 2 , Cs 2 CO 3 and SPhos as the ligand, efficiently delivers chromeno[3,4-b]pyrrol-4-(3H)-ones 40 (Scheme 12). Aliphatic amines were successfully employed.…”

Section: Synthesis Of Coumarin-linked and Coumarin-fused Heterocyclesmentioning

confidence: 99%

“…Recently an efficient palladium-catalyzed domino C-N coupling/hydroamination reaction of coumarin derivatives 39 and amines 29 has been developed by Langer. 43 Thus, the reaction of 3-bromo-4-ethynyl-coumarin derivatives 39 with amines 29, performed using Pd(OAc) 2 , Cs 2 CO 3 and SPhos as the ligand, efficiently delivers chromeno[3,4-b]pyrrol-4-(3H)-ones 40 (Scheme 12). Aliphatic amines were successfully employed.…”

Section: Synthesis Of Coumarin-linked and Coumarin-fused Heterocyclesmentioning

confidence: 99%

Coumarin heterocyclic derivatives: chemical synthesis and biological activity

et al. 2015

View full text Add to dashboard Cite

show abstract

Synthesis of pyrrolocoumarins via Pd-catalyzed domino C–N coupling/hydroamination reactions

Cited by 19 publications

References 28 publications

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

Coumarin heterocyclic derivatives: chemical synthesis and biological activity

Contact Info

Product

Resources

About

Synthesis of pyrrolocoumarins via Pd-catalyzed domino C–N coupling/hydroamination reactions

Cited by 19 publications

References 28 publications

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolo­coumarins

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolo­coumarins

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

Coumarin heterocyclic derivatives: chemical synthesis and biological activity

Contact Info

Product

Resources

About

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins