Activator free diastereoselective 1,3-dipolar cycloaddition: a quick access to coumarin based spiro multi heterocyclic adducts

Thadem, Nagender; Rajesh, Manda; Das, Saibal

doi:10.1039/d1ra05070b

Cited by 5 publications

(2 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The conformational constraints and juxtaposition of reactants frequently lead to readily cycloaddition with complete or very high selectivity. For the reasons mentioned above, 1,3-DCR has been described as "the single most important method for the construction of heterocyclic five-membered rings" (Jørgensen, 2002;Gupta and Khurana., 2019;Thadem et al, 2021). Major hurdles that regularly occur in organic synthesis are atom economy and novel and efficient reactions, which can answer both the ecological aspect and target-oriented synthesis (de Graaff et al, 2012;Lledó et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Graphene Oxide Catalyzed Synthesis of Fused Chromeno Spiro Pyrrolidine Oxindoles via Tandem Decarboxylation and 1,3-Dipolar Cycloaddition

2022

View full text Add to dashboard Cite

A short and efficient multicomponent sequence for synthesizing fused novel polyheterocyclic chromeno spiro-pyrrolidine oxindoles via 1,3-dipolar cycloaddition reaction mediated by reactive azomethine ylides catalyzed by the Graphene Oxide (GO) is reported herein. This approach was utilized for synthesizing fused polyheterocyclic spiro-pyrrolothiazole and spiro-pyrrole oxindoles with yields ranging from good to excellent. A heterogeneous GO catalyst with an ultra-low catalytic loading of 0.05 wt% could proficiently catalyze the reaction without the formation of any side products and can also be visualized by the formation of solid mass in the reaction flask. The methodology is green in nature and the products were isolated by simple filtration without the use of any chromatographic techniques.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Graphene Oxide Catalyzed Synthesis of Fused Chromeno Spiro Pyrrolidine Oxindoles via Tandem Decarboxylation and 1,3-Dipolar Cycloaddition

2022

View full text Add to dashboard Cite

show abstract

Substrate-Controlled Regioselectivity Switchable [3 + 2] Annulations To Access Spirooxindole Skeletons

Wang

Chen

et al. 2022

J. Org. Chem.

View full text Add to dashboard Cite

The additive-free [3 + 2] annulation from isatins, amino acids with 2-styrylbenzoxazoles, was described, providing a series of functional and structurally complex 3,3′-pyrrolidinyl-spirooxindole derivatives containing four contiguous and two quaternary stereogenic centers in high yields (up to 95%) and excellent diastereoselectivities (up to >25:1 dr). Interestingly, the reaction exhibits switchable regioselectivity depending on the substrate of amino acids. With proline or thioproline as the substrate, the reaction afforded α-regioselective spirooxindole skeletons. In contrast, when piperidine acid is the substrate, the reaction provided γ-regioselective spirooxindole skeletons.

show abstract

Acylsilane Directed Rh-Catalyzed Arene C–H Alkylation with Maleimides and Visible-Light-Induced Siloxycarbene-Amide Cyclization: [3 + 2] Carbo-Annulation in Ru Catalysis

et al. 2023

Self Cite

View full text Add to dashboard Cite

We herein demonstrate the acylsilane-directed Rh-catalyzed arene C−H bond alkylation with maleimides. The resulting derivatives were utilized in visible-light-induced intramolecular siloxycarbene-amide cyclization for the synthesis of new tricyclic γ-lactams. In parallel, we also harnessed the same acylsilane and maleimide units through [3 + 2] carbo-annulation by using Ru-catalysis. A wide range of maleimides and aroylsilanes were used to establish the broadness of these transformations.

show abstract

Activator free diastereoselective 1,3-dipolar cycloaddition: a quick access to coumarin based spiro multi heterocyclic adducts

Abstract: A formal diastereoselective decarboxylative 1,3-dipolar cycloaddition of azomethine ylide and coumarins is achieved for the synthesis of spiro multi heterocyclic adducts without engaging any catalyst or activator in good yields.

Cited by 5 publications

References 56 publications

Graphene Oxide Catalyzed Synthesis of Fused Chromeno Spiro Pyrrolidine Oxindoles via Tandem Decarboxylation and 1,3-Dipolar Cycloaddition

Graphene Oxide Catalyzed Synthesis of Fused Chromeno Spiro Pyrrolidine Oxindoles via Tandem Decarboxylation and 1,3-Dipolar Cycloaddition

Substrate-Controlled Regioselectivity Switchable [3 + 2] Annulations To Access Spirooxindole Skeletons

Acylsilane Directed Rh-Catalyzed Arene C–H Alkylation with Maleimides and Visible-Light-Induced Siloxycarbene-Amide Cyclization: [3 + 2] Carbo-Annulation in Ru Catalysis

Contact Info

Product

Resources

About