Regio- and stereoselective synthesis of functionalized and fused heterocycles from Morita–Baylis–Hillman adducts of dicyclopentadienone

Suresh, Alati; Lal, Sohan; Namboothiri, Irishi N. N.

doi:10.1039/d1ob02505h

Cited by 4 publications

(2 citation statements)

References 65 publications

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“…31 The applicability of this reaction lies in the commercial availability of the starting materials, its high atom economy, it does not require a metallic catalyst, and it works under mild conditions. 32 Furthermore, the resulting Morita-Baylis-Hillman adducts can be used as building block for the synthesis of natural products, biologically active compounds, 33 and functional molecules. 34 All the considerations mentioned above, makes the Morita-Baylis-Hillman a good candidate for automatized using MIK-I.…”

Section: Morita-baylis-hillman Reactionmentioning

confidence: 99%

Building C-C bonds using a cheap automated synthesis platform

Flores-Ortiz,

Gutiérrez-Márquez,

Mier-Jiménez

et al. 2023

Preprint

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The formation of C-C bonds through automated synthesis platforms seeks to accelerate the preparation of molecules, simplify the operational processes, and reduce the human time required for synthesis. Here, we report C-C bond formation using a low-cost automated synthesis platform that seeks to democratize automated organic synthesis. MIK-I can run reactions widely used in organic chemistry: Claisen-Schmidt condensations, Suzuki-Miyaura coupling, Knoevenagel condensations, and Morita-Baylis-Hillman reactions, showing similar yields obtained manually, which highlights the potential of this platform for the synthesis of building blocks.

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Section: Morita-baylis-hillman Reactionmentioning

confidence: 99%

Building C-C bonds using a cheap automated synthesis platform

Flores-Ortiz,

Gutiérrez-Márquez,

Mier-Jiménez

et al. 2023

Preprint

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“…MBH adducts contain the structural moieties of allylic alcohols or amines, Michael acceptors, and electron-withdrawing groups, which makes them valuable substrates for various types of reactions such as Michael addition, allylic substitution, cycloaddition reaction, Friedel-Crafts reaction, Claisen rearrangement, etc. [ 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 ]. Based on our previous studies of 1,3-dipolar cycloaddition, Michael addition of azomethine ylides and azomethine imines and palladium-catalyzed tandem reaction to construct 3,3-disubstituted indolinones [ 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 ], herein we report the mono-/diallylation of isatin N , N ′-cyclic azomethine imines from the condensation of isatin and pyrazolidones with MBH carbonates.…”

Section: Introductionmentioning

confidence: 99%

DABCO-Catalyzed Mono-/Diallylation of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates

Wang

Li²,

Yang

et al. 2023

Molecules

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Allylation of N-unsubstituted isatin N,N′-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1–10 mol% DABCO in DCM at room temperature, rapidly gave N-allylated and N, β-diallylated isatin N,N′-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The reaction features mild reaction conditions, easily practical operation, and short reaction times in most cases. Furthermore, the alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through the [3+2] or [3+3]-cycloaddition with maleimides or Knoevenagel adducts.

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Synthesis, Characterization and Energetic Properties of Hydroxymethyl‐Bishomocubanone Derivatives

Lal,

Rao Cheekatla,

Suresh

et al. 2024

Chemistry A European J

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The present work reports synthesis, characterization and theoretical insights on novel hydroxymethyl‐bishomocubanone derivatives. Twelve new bishomocubanes (BHCs) were synthesized and fully characterized by various spectroscopic techniques and single crystal X‐ray analysis. The densities of the title compounds were found in the range of 1.34‐1.59 g/cm3. Density‐functional theory (DFT) based calculations at B3LYP/6‐311++G(d,p) level of theory were performed on ten selected BHC based cage compounds. Propulsive and ballistic properties of newly synthesized hydroxymethyl‐bishomocubanone derivatives in solid and liquid propulsion systems were calculated, and the results suggested that these compounds are superior to conventional fuel RP1 and binder HTPB. The detonation parameters revealed that these compounds are not explosive in nature and safe to use as solid propellants. Furthermore, kinetic and thermal stabilities of the title compounds were determined by HOMO‐LUMO energy gap, ESP maps, impact sensitivity (h50) and bond dissociation energies (BDEs) followed by thermogravimetric analysis (TGA) and differential thermogravimetry analysis (DTA). Three compounds, a dinitroazide (Isp,vac= 310.98s), a dinitrate (Isp,vac = 309.51s), and a dinitronitrate (Isp,vac= 309.20s) were found to be excellent candidates for volume limited applications.

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Regio- and stereoselective synthesis of functionalized and fused heterocycles from Morita–Baylis–Hillman adducts of dicyclopentadienone

Abstract: An efficient protocol for the Morita-Baylis-Hillman (MBH) reaction of dicyclopentadienone using CTAB has been developed. The MBH adduct was subsequently transformed to its acetate and bromide derivatives. The 1,3-bielectrophilic character...

Cited by 4 publications

References 65 publications

Building C-C bonds using a cheap automated synthesis platform

Building C-C bonds using a cheap automated synthesis platform

DABCO-Catalyzed Mono-/Diallylation of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates

Synthesis, Characterization and Energetic Properties of Hydroxymethyl‐Bishomocubanone Derivatives

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