1,3-Dipolar Cycloaddition of Ethyl Diazoacetate with (E)-3-Arylidenechroman-4-ones. A New Access to Spirocyclopropane Derivatives

Ciamala, Kabula; Jelizi, Hanene; Rammah, Mohamed M.; Wannassi, Nadia; Monnier-Jobé, Karin; Rousselin, Yoann; Kubicki, Marek M.; Strohmann, Carsten

doi:10.3987/com-11-12415

Cited by 9 publications

(2 citation statements)

References 22 publications

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“…Interestingly, when the reaction was conducted at 50 °C, the major product was 2‐pyrazoline 16 , with only trace quantities of 15 detected (entry 5). 2‐Pyrazoline 16 likely derives from 1‐pyrazoline intermediate 14 undergoing a 1,3‐prototropic shift at lower temperature, in preference to thermolysis [9f] . While we postulated that 1‐pyrazoline 14 was an intermediate leading to product 16 , the former could not be observed, presumably because it rapidly tautomerised to 2‐pyrazoline 16 at lower temperature.…”

Section: Resultsmentioning

confidence: 67%

“…Thermal decompositions of 1‐pyrazolines to produce cyclopropanes are well‐known, [9] however, the mechanistic nuances of thermal nitrogen extrusion are not as well‐understood as equivalent aspects of the photolytic process [9b,10] . Radical, [9b,f,11] ionic, [9e,12] and concerted mechanisms [9d,13] have been invoked to explain the varying regio‐ and stereochemical outcomes of 1‐pyrazoline decompositions. Thus, the precise decomposition mechanism may be substrate dependent [13] …”

Section: Resultsmentioning

confidence: 99%

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Dipole‐Transmissive 1,3‐Dipolar Cycloadditions for the Rapid Construction of Polycyclic N‐Heterocycles: Synthetic and Mechanistic Investigations

Henneveld

Shiri

Ariafard

et al. 2023

Chemistry A European J

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The investigation of distinctive dipole‐transmissive dipolar cycloaddition (DTDC) methodology and the formalisation of this concept is reported. A DTDC procedure was able to be developed by taking advantage of the structural complementarity of azide and diazoalkane 1,3‐dipoles. Intramolecular azide‐alkene 1,3‐DCs followed by spontaneous dipole transmission upon work‐up furnished intermediate α‐diazoisoindole and α‐diazoisoquinoline substrates bearing the key secondary diazoalkane 1,3‐dipole. N‐Derivatisation of the intermediate α‐diazoisoindole and α‐diazoisoquinolines with a tethered secondary dipolarophile followed by a subsequent 1,3‐DC allowed for rapid construction of a range of functionalised polycyclic N‐heterocycles. Integrated experimental and theoretical studies established requirements for product formation and revealed the likely mechanistic basis of divergent reactivity observed.

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Section: Resultsmentioning

confidence: 67%

Section: Resultsmentioning

confidence: 99%

Dipole‐Transmissive 1,3‐Dipolar Cycloadditions for the Rapid Construction of Polycyclic N‐Heterocycles: Synthetic and Mechanistic Investigations

Henneveld

Shiri

Ariafard

et al. 2023

Chemistry A European J

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3‐Arylidene‐4‐Chromanones and 3‐Arylidene‐4‐Thiochromanones: Versatile Synthons towards the Synthesis of Complex Heterocycles

2022

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Heterocyclic compounds are well-known for their use in the synthesis of drugs and drug intermediates. This review provides a systematic survey on the chemical synthesis of complex heterocyclic compounds containing multistereocentres using 3-arylidene-4-chromanones in the last two decades. Regioselective and stereoselective synthesis of complex heterocycles involving 3-arylidene-chromanones and 3-arylidene-thiochormanones are dealt under various reaction headings such as epoxidation, Michael addition, 1,3dipolar cycloaddition, [3 + 2] and [4 + 2] cycloaddition, Diels-Alder reaction, sulfa-Michael/aldol cascade reactions, asym-metric synthesis employing bifunctional catalysts, chiral phase-transfer catalysts, chiral squaramide catalysts, etc. These synthetic highlights demonstrate the utility of 3arylidene-4-chromanones and 3-arylidene-thiochormanones as versatile synthons for rapid assemblage of complex condensed heterocyles and spiro-fused heterocycles towards the development of pharmaceutically active compounds. A brief highlight on the synthetic methods of 3-arylidene-4chromanone derivatives is also dealt. This review creates a platform for further improvement on the skeletal design of potential drug candidates.

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ChemInform Abstract: 1,3‐Dipolar Cycloaddition of Ethyl Diazoacetate with (E)‐3‐Arylidenechroman‐4‐ones. A New Access to Spirocyclopropane Derivatives.

et al. 2012

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1,3-Dipolar Cycloaddition of Ethyl Diazoacetate with (E)-3-Arylidenechroman-4-ones. A New Access to Spirocyclopropane Derivatives

Abstract: International audienc

Cited by 9 publications

References 22 publications

Dipole‐Transmissive 1,3‐Dipolar Cycloadditions for the Rapid Construction of Polycyclic N‐Heterocycles: Synthetic and Mechanistic Investigations

Dipole‐Transmissive 1,3‐Dipolar Cycloadditions for the Rapid Construction of Polycyclic N‐Heterocycles: Synthetic and Mechanistic Investigations

3‐Arylidene‐4‐Chromanones and 3‐Arylidene‐4‐Thiochromanones: Versatile Synthons towards the Synthesis of Complex Heterocycles

ChemInform Abstract: 1,3‐Dipolar Cycloaddition of Ethyl Diazoacetate with (E)‐3‐Arylidenechroman‐4‐ones. A New Access to Spirocyclopropane Derivatives.

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