Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes

Doraghi, Fatemeh; Mohaghegh, Farid; Qareaghaj, Omid Hosseinchi; Larijani, Bagher; Mahdavi, Mohammad

doi:10.1039/d3ra01778h

Cited by 4 publications

(1 citation statement)

References 130 publications

(116 reference statements)

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“…[2] For instance, their reactivity seamlessly fits into iminium [3] and enamine [4] catalysis, leading to the stereoselective assembly of molecular frameworks that otherwise might be inaccessible. Likewise, both are pivotal in synthesizing heterocyclic compounds, [5] particularly those incorporating nitrogen. [6] This specific facet places these compounds at the core of organic and pharmaceutical synthetic routes, where their diverse reactivity facilitates the development of unique and consolidated strategies.…”

Section: Introductionmentioning

confidence: 99%

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

Behera,

Kanti Bera,

Basoccu

et al. 2024

Adv Synth Catal

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Our research has demonstrated that mechanochemical activation is more effective with solid reagents. We have showcased the practicality of Bertagnini's salts, also called aldehyde‐bisulfite adducts, which are crystalline, simplifying preparation and storage. These salts are stable substitutes for liquid aldehydes and ketones that have been effectively employed in reductive amination, synthesizing aza‐heterocycles and hydrazones within mechanochemistry. The technique's effectiveness broadens the substrate scopes, simplifies purification, reduces reaction times, and delivers good product yields. Additionally, the thermal stability of the bisulfite adducts has been confirmed through TGA (Thermogravimetric analysis) analysis.

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Section: Introductionmentioning

confidence: 99%

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

Behera,

Kanti Bera,

Basoccu

et al. 2024

Adv Synth Catal

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N‐Heterocyclic Carbene Catalyzed Reactions Involving Acetylenic Breslow and/or Acylazolium as Key Intermediates

He,

Chen,

Jiang

et al. 2024

The Chemical Record

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N‐heterocyclic carbene (NHC) organocatalysis has been developed as a powerful tool in modern synthetic chemistry. NHC catalytic activation of ynals and alkynoic acid derivatives provided versatile reactions that involve acetylenic Breslow and/or acylazolium as key intermediates, and diverse transformations have been established for access to molecules with unique skeletons in efficient fashions. Herein we summarize the recent achievements in NHC‐catalyzed reactions involving acetylenic Breslow and/or acylazolium intermediates. Different reactions belonging to three catalytic modes, including (1) conjugate additions to acetylenic Breslow derived α,β‐unsaturated acylazolium intermediates, (2) β‐umpolung of ynals via acetylenic Breslow intermediates, and (3) conjugate additions to acetylenic acylazolium intermediates, are emphasized with examples and plausible mechanisms cited to guide a better understanding.

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Six-membered ring systems: With O and/or S atoms

Santos,

Silva

2024

Progress in Heterocyclic Chemistry

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Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes

Abstract: Preparation of many kinds of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes were investigated in recent years. In this review, the synthesis of bioactive heterocycles using by substituted alkynyl aldehydes is highlighted.

Cited by 4 publications

References 130 publications

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

N‐Heterocyclic Carbene Catalyzed Reactions Involving Acetylenic Breslow and/or Acylazolium as Key Intermediates

Six-membered ring systems: With O and/or S atoms

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