Microwave assisted synthesis of β-keto thioethers and furan derivatives by thiol directed multicomponent reactions

Jana, Asim Kumar; Bhaumick, Prabhas; Choudhury, Lokman H.

doi:10.1039/d0nj00587h

Cited by 8 publications

(3 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This combination of functional and basis set has been used to determine the conformational preferences of other halogenated ketones . This orientation of the substituents in the lowest-energy conformer, which promotes hyperconjugative interactions of σ C–X → π* C–O , is often observed in computational studies, solution-phase experiments, and solid-phase structures of α-chloroketones, − α-bromoketones, − and α-thiophenyl ketones. − The greater preference for conformation 9 when X = Br and X = SPh compared to that when X = Cl can be attributed to the carbon–bromine bond and the carbon–sulfur bond being better electron donors than the carbon–chlorine bond. − …”

Section: Resultsmentioning

confidence: 99%

Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides

et al. 2022

View full text Add to dashboard Cite

The addition of the highly reactive reagent allylmagnesium halide to α-substituted acyclic chiral ketones proceeded with high stereoselectivity. The stereoselectivity cannot be analyzed by conventional stereochemical models because these reactions do not conform to the requirements of those models. Instead, the stereoselectivity arises from the approach of the nucleophile to the most accessible diastereofaces of the lowest-energy conformations of the ketones. High stereoselectivity is expected, and the stereochemical outcome can be predicted, with conformationally biased ketones that have sterically distinguishable diastereofaces wherein only one face is accessible for nucleophilic addition. The conformations of the ketones can be determined by a combination of computational modeling and, in some cases, structure determination by X-ray crystallography.

show abstract

Section: Resultsmentioning

confidence: 99%

Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Both aryl thioethers and 2-phenyl-4H-furo[3,2- c ] chromen-4-ones have diverse medicinal properties. Considering their importance and in continuation of our work on the synthesis of fused heterocycles as well as new methodology development, we shifted our attention to the development of a straightforward method for the synthesis of hybrid molecules having thioethers linked with 2-phenyl-4H-furo[3,2- c ] chromen-4-ones from the readily available starting materials. For our initial study, phenylglyoxal monohydrate ( 1a ), 4-hydroxycoumarin ( 2a ), and 4-chlorothiophenol ( 3d) were chosen.…”

Section: Results and Discussionmentioning

confidence: 53%

“…mp 168−172 °C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.17 (d,J = 8.0 Hz,2H,Ar),7.98 (d,J = 8.0 Hz,1H,Ar),7.56 (t,J = 8.0 Hz,1H,Ar),2H,Ar),4H,Ar),7.16 (t, J = 8.0 Hz, 1H, Ar), 7.02 (d,J = 8.0 Hz,2H,Ar),3.89 (s,3H,OCH 3 ). 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 160.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Sc(OTf)₃-Mediated One-Pot Synthesis of Coumarin-Fused Furans: A Thiol-Dependent Reaction for the Easy Access of 2-Phenyl-4H-furo[3,2-c]chromen-4-ones

et al. 2022

Self Cite

View full text Add to dashboard Cite

Herein, we report a simple and efficient method for the preparation of novel thioether-linked coumarin-fused furans from the one-pot three-component reaction of arylglyoxal, 4-hydroxycoumarin, and various aromatic thiols in the presence of Sc(OTf)3 as a catalyst. This methodology is also applicable to cyclic 1,3-dicarbonyls such as cyclohexane-1,3-dione and dimedone. Depending upon the thiols, this methodology can either give a three-component thioether-linked coumarin-fused furan (4) or a two-component furocoumarin product (5). Wide substrate scope, good to excellent yields, and products having more than one pharmaceutically important motif are the salient features of this methodology.

show abstract

Metal‐Free Synthesis of Pyrimidine and Naphthoquinone‐Fused Pyrroles from Arylglyoxal‐Based Domino Reactions

et al. 2023

Self Cite

View full text Add to dashboard Cite

Herein we report acid mediated two and three‐component domino reactions of cyclic enamines such as 2‐amino‐1,4‐naphthoquinone, and 6‐amino‐1,3‐dimethyluracil with arylglyoxals for the synthesis of diverse fused pyrroles. The two‐component reaction of arylglyoxal and 2‐amino‐1,4‐naphthoquinone in the acetic acid medium provided substituted naphthoquinone‐fused pyrroles tethered with hydroxyl and aryl substituents. On the other hand, under similar reaction conditions, the reaction of phenylglyoxal with 6‐amino‐1,3‐dimethyluracil provided an unusual bipyrrolopyrimidine with a quaternary carbon center following a domino reaction involving the formation of five new sigma bonds in one‐pot. Interestingly, the reaction of arylglyoxals with 6‐amino‐1,3‐dimethyluracil in ethanol medium in the presence of 10‐mol% PTSA provided a three‐component product having pyrimidine fused pyrrole linked with 6‐aminouracil moiety. We have also developed a three‐component reaction of 2‐amino‐1,4‐naphthoquinone, arylglyoxals, and 4‐hydroxy‐1‐methylquinolin‐2(1H)‐one for the synthesis of naphthoquinone‐fused pyrroles linked with hydroxyquinoline derivatives.

show abstract

Microwave assisted synthesis of β-keto thioethers and furan derivatives by thiol directed multicomponent reactions

Abstract: A series of β-keto thioethers tethered with cyclic-1,3-dicarbonyls (4) and a tetra-substituted furan derivative (5) has been prepared by multicomponent reaction under microwave heating conditions.

Cited by 8 publications

References 29 publications

Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides

Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides

Sc(OTf)₃-Mediated One-Pot Synthesis of Coumarin-Fused Furans: A Thiol-Dependent Reaction for the Easy Access of 2-Phenyl-4H-furo[3,2-c]chromen-4-ones

Metal‐Free Synthesis of Pyrimidine and Naphthoquinone‐Fused Pyrroles from Arylglyoxal‐Based Domino Reactions

Contact Info

Product

Resources

About

Microwave assisted synthesis of β-keto thioethers and furan derivatives by thiol directed multicomponent reactions

Abstract: A series of β-keto thioethers tethered with cyclic-1,3-dicarbonyls (4) and a tetra-substituted furan derivative (5) has been prepared by multicomponent reaction under microwave heating conditions.

Cited by 8 publications

References 29 publications

Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides

Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides

Sc(OTf)3-Mediated One-Pot Synthesis of Coumarin-Fused Furans: A Thiol-Dependent Reaction for the Easy Access of 2-Phenyl-4H-furo[3,2-c]chromen-4-ones

Metal‐Free Synthesis of Pyrimidine and Naphthoquinone‐Fused Pyrroles from Arylglyoxal‐Based Domino Reactions

Contact Info

Product

Resources

About

Sc(OTf)₃-Mediated One-Pot Synthesis of Coumarin-Fused Furans: A Thiol-Dependent Reaction for the Easy Access of 2-Phenyl-4H-furo[3,2-c]chromen-4-ones