Catalyst-Controlled Divergent Synthesis of 2<i>H</i>-Chromenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Quinones

Deshwal, Shalu; Davas, Daksh Singh; Bhardwaj, Srashti; Vaitla, Janakiram

doi:10.1021/acs.orglett.3c03894

Org. Lett.

2024

DOI: 10.1021/acs.orglett.3c03894

|View full text |Cite

Catalyst-Controlled Divergent Synthesis of 2H-Chromenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Quinones

Shalu Deshwal,

Daksh Singh Davas,

Srashti Bhardwaj

et al.

Abstract: Herein, we report the synthesis of 2H-chromenes via catalystcontrolled highly regioselective [3 + 3] annulation of vinyl sulfoxonium ylides with quinones. Under boron-catalyzed conditions, the reaction between the ylide and quinone resulted in the formation of 2H-chromene-4carboxylates. In contrast, a different mechanistic pathway was observed when utilizing a Ru(II) catalytic system, which led to the formation of 2Hchromene-2-carboxylates through a furan intermediate.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article5

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 10 publications

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

Pratap,

Shukla,

Giri

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

Here we report a transition metal– and oxidant–free annulation cascade method for the synthesis of chromeno–isoxazoles. The annulation reaction involves easily accessible starting materials, 3‐nitro‐2H‐chromene and α‐chloro aldehyde, yielding the structurally intriguing framework, chromeno[3,4‐c]isoxazoles employed by tripotassium phosphate as a base. The isoxazole ring construction over the 2H–chromene unit is believed to occur via a series of multiple reaction sequences. Here, the enolate generation/Michael addition/C–Cl bond cleavage/oxy–anionic addition to reactive tethered‐aldehyde/deformylation via retro– C–C and N–O bond cleavages are the most possible sequences which furnish the desired end–product in good chemical yields. The multiple reaction sequences occur in one‐pot at mild conditions, supported by experimental results and a few control experiments including DFT studies. This process exhibits a broad substrates scope illustrating good functional group compatibility towards both the nitrochromenes and aldehydes, and thus prove to be a general and efficient protocol for the synthesis of chromeno[3,4–c]isoxazoles. Overall, the use of nitrochromene as the limiting reagent, noteworthy functional group tolerance, scalability including great applications like chiral pool strategy towards the synthesis of enantioenriched chromeno‐isoxazole are the additional features.

show abstract

K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

Pratap,

Shukla,

Giri

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

He,

Huang,

Huang

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing o-hydroxyphenyl group. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 3-(o-hydroxyarylidene)indolin-2-ones in tetrahydrofuran at 60 °C resulted in unique functionalized spiro [cyclobuta[c]chromene-1,3′-indolines] in good yields and with high diastereoselectivity. However, the similar three-component reaction with 2-(5-halo-2-hydroxyarylidene)indolin-2-ones afforded unexpected chain products in satisfactory yields. In addition, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 2-(o-hydroxyarylidene)-1,3-indanediones in tetrahydrofuran at 60 °C resulted in complex indeno[2′,1′:5,6]pyrano [3,4-c]chromene derivatives in high yields and with high diastereoselectivity.

show abstract

Carbene-Catalyzed [3 + 3] Annulation of Enals and Vinyl Sulfoxonium Ylides

Feng,

Zhang,

Liu

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Catalyst-Controlled Divergent Synthesis of 2H-Chromenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Quinones

Cited by 10 publications

References 30 publications

K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

Carbene-Catalyzed [3 + 3] Annulation of Enals and Vinyl Sulfoxonium Ylides

Contact Info

Product

Resources

About

Catalyst-Controlled Divergent Synthesis of 2H-Chromenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Quinones

Cited by 10 publications

References 30 publications

K3PO4–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

K3PO4–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

Carbene-Catalyzed [3 + 3] Annulation of Enals and Vinyl Sulfoxonium Ylides

Contact Info

Product

Resources

About

K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences