Azomethine ylide [3 + 2]-cycloaddition of 3-alkylidene-7-aza-2-indolone: Synthesis of 3,3′-dispiropyrrolidine- and 3,3′-dispiropyrrolizidine bis 7-aza-2-oxindoles

Preethi, R.; Kannadasan, Sathananthan; Shanmugam, P.

doi:10.1016/j.tetlet.2023.154448

Cited by 4 publications

(1 citation statement)

References 22 publications

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“…By adding the multiple bond system to a three-atom component (TAC), which is a neutral species consisting of three closely connected heavy nuclei with a minimum electron density of 8 electrons, these reactions have proven highly valuable in synthesizing vemembered heterocyclic compounds. [42][43][44][45] In 2013, Moncef Msadek and co-workers developed a successful strategy for creating a unique category of extensively substituted pyrazole structures 5. They achieved this through a 1,3-cycloaddition reaction involving aurone 1 and aryl diazomethane 3 (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

A concise update on the synthetic transformation of aurones via asymmetric cycloaddition, annulation, and Michael/Mannich reactions

John,

George,

Radhakrishnan

2024

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

A concise update on the synthetic transformation of aurones via asymmetric cycloaddition, annulation, and Michael/Mannich reactions

John,

George,

Radhakrishnan

2024

RSC Adv.

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Synthesis of 3‐Spiro Cycloalkenes Fused 7‐Aza‐2‐indalones from 3,3′‐di‐ or N,3,3′‐tri‐ allyl/homoallyl/pentenyl 7‐Aza‐2‐indalones via Ring Closing Metathesis using Grubbs‐II Catalyst

Chirranjeevi Padmashrija,

Kannadasan,

Shanmugam

2023

ChemistrySelect

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A facile and efficient synthesis of 3‐spiro cycloalkene fused 7‐aza‐2‐indalones from 3,3′‐di‐ or N,3,3′‐tri‐ allyl/homoallyl/pentenyl 7‐aza‐2‐indalones via ring‐closing metathesis (RCM) using Grubbs‐II catalyst has been achieved. The scope of the reaction has been demonstrated by synthesizing spiro products of various ring sizes (n=5, 7, and 18), utilizing 2‐indalone/7‐azaindalone and various alkenylation agents such as allyl/homoallyl/pentenyl bromides as substrates. In addition to usual RCM products, a cross metathesis (CM) product was observed when the substrate was N,3,3′‐triallylated derivative from 2‐indalone. Notably, a macrocyclic, 18‐membered bis‐spirodiene of N‐methyl‐7‐azaindalone was observed by means of intermolecular ring‐closing metathesis (RCM‐RCM). Also, Structures of a few representative spiro‐annulated products were evidenced with single crystal XRD analysis. Furthermore, a plausible mechanism for the products is discussed.

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One‐Pot Triple and Mixed Double Michael Addition of Activated Alkenes to 2‐Oxindole and 7‐Aza‐2‐Oxindole: Synthesis of C‐3/N‐Functionalized Carbon Rich 2‐Oxindole and 7‐Aza‐2‐Oxindole Derivatives

Kavitha Preethi,

Kannadasan,

Shanmugam

2024

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A simple, efficient, and atom‐economical, one‐pot triple Michael Addition of activated alkenes to 2‐oxindole, 7‐aza‐2‐ indolone, and N‐methyl‐5‐bromo‐7‐aza‐2‐indolone has been developed. Significantly, multifunctionalities have also been achieved via one‐pot mixed Michael addition using the equimolar amount of two different activated alkenes. The reaction provided C‐3 and N‐functionalized carbon‐rich 7‐aza‐2‐oxindole derivatives. The scope of the reaction using diverse activated alkenes has been tested to provide the title compounds. The structure of the representative compounds has been established by the XRD method. Synthetic transformation of representative compounds is demonstrated to provide the respective 3‐spirooctane‐2‐oxindole derivatives in excellent yield. A plausible mechanism for cyclization is provided.

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Azomethine ylide [3 + 2]-cycloaddition of 3-alkylidene-7-aza-2-indolone: Synthesis of 3,3′-dispiropyrrolidine- and 3,3′-dispiropyrrolizidine bis 7-aza-2-oxindoles

Cited by 4 publications

References 22 publications

A concise update on the synthetic transformation of aurones via asymmetric cycloaddition, annulation, and Michael/Mannich reactions

A concise update on the synthetic transformation of aurones via asymmetric cycloaddition, annulation, and Michael/Mannich reactions

Synthesis of 3‐Spiro Cycloalkenes Fused 7‐Aza‐2‐indalones from 3,3′‐di‐ or N,3,3′‐tri‐ allyl/homoallyl/pentenyl 7‐Aza‐2‐indalones via Ring Closing Metathesis using Grubbs‐II Catalyst

One‐Pot Triple and Mixed Double Michael Addition of Activated Alkenes to 2‐Oxindole and 7‐Aza‐2‐Oxindole: Synthesis of C‐3/N‐Functionalized Carbon Rich 2‐Oxindole and 7‐Aza‐2‐Oxindole Derivatives

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