Synthesis and Reactivity of 4-Amino-Substituted Furfurals

Erdenebileg, Uranbaatar; Høstmark, Inger; Polden, Karina; Sydnes, Leiv K.

doi:10.1021/jo4026308

Cited by 19 publications

(21 citation statements)

References 20 publications

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“…Yield: 18%. 1 13 C NMR (100 MHz, CDCl3) δ 172. 4, 161.0, 136.8, 133.7, 130.2, 129.4, 123.1, 122.8, 52.7, 37.9, 31.6, 29.5, 28.9, 28.5, 22.5, 14.0 The title compound was prepared according to the general procedure.…”

Section: (E)-methyl 2-(pent-1-enyl)-3-phenyl-2h-azirine-2-carboxylatementioning

confidence: 99%

“…Yield: 97%. 1 13 C NMR (100 MHz, CDCl3) δ 183. 5, 164.8, 144.7, 134.3, 129.9, 128.7, 127.8, 121.2, 62.7, 38.8, 32.7, 29.5, 29.1, 28.0, 26.4; HRMS (ESI) m/z [M+H] + : Calcd for C18H22N3O2: 312.1712.…”

Section: (Z)-1-cycloheptylidene-3-diazo-4-(methoxyimino)-4-phenylbutamentioning

confidence: 99%

“…Sydnes reported that a novel access to 4-amino-substituted furfurals 1 from γ-hydroxy-α, β-unsaturated acetylenic ketones 3 through reaction with secondary amines, followed by treatment with acid in a mixture of THF and water (Scheme 1.1, route b). 13 Enynedione compounds 4 were successfully applied to construct trisubstituted furans 1 (Scheme 1.1, route c) through intramolecular cyclization. 14 In 2004, Larock and co-workers discovered the utilization of 2-(1-alkynyl)-2-alkene-1-ones 5 as common substrates to prepare substituted furans via gold-catalyzed cyclization (Scheme 1.1, route d).…”

Section: Introductionmentioning

confidence: 99%

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Expedient synthesis of heterocycles and methyl sulfonyl compounds via C-X BONDS (X = O, N, S) construction

Jiang¹

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CONSTRUCTION 2.3 Nickel(II)-Catalyzed Synthesis of Fully Substituted Pyrroles 2.4 Conclusion 2.5 Experimental Section iv CHAPTER 3. NOVEL APPROACHES TO MULTI-SUBSTITUTED PYRIDINES BY RING-EXPANSION OF 2H-AZIRINES 3.1 OVERVIEW 3.2 Rhodium(II)-Catalyzed Synthesis of Pyridines through Amination of sp 3 C-H bond 3.3 Transition-Metal-Free Synthesis of Pyridines through Amination of sp 2 C-H bond 3.4 Conclusion 3.5 Experimental Section CHAPTER 4. CATALYTIC AND DIRECT METHYL SULFONYLATION OF ALKENES AND ALKYNES USING METHYL SULFONYL RADICAL GENERATED FROM DMSO, DIOXYGEN AND COPPER SYSTEM 4.1 OVERVIEW 4.2 Synthesis of β-Keto Methyl Sulfones by Methyl Sulfonylation of Alkenes with DMSO 4.3 Synthesis of (E)-Vinyl Methyl Sulfones by Methyl Sulfonylation of Alkynes with DMSO 4.4 Conclusion 4.5 Experimental Section

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Section: (E)-methyl 2-(pent-1-enyl)-3-phenyl-2h-azirine-2-carboxylatementioning

confidence: 99%

Section: (Z)-1-cycloheptylidene-3-diazo-4-(methoxyimino)-4-phenylbutamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Expedient synthesis of heterocycles and methyl sulfonyl compounds via C-X BONDS (X = O, N, S) construction

Jiang¹

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“…Furan based π-conjugated materials have been attained more interests during the past decade, because furan containing OSMs are more stable and potentially applicable in modern era optoelectronic devices like organic field effect transistor (OFETs), organic solar cells, organic light emitting transistor (OLETs), and organic light-emitting diodes (OLEDs) [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

et al. 2015

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The present study spotlights the designing of new derivatives of 2,7-bis (4-octylphenyl) naphtho [2,1-b:6,5-b'] difuran (C8-DPNDF) by substituting the alkyl groups (methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl groups) at para position. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods are employed to optimize the molecular structures in ground and first excited states, respectively. Several electro-optical properties including hole/electron reorganization energies (λh/λe), electron affinities (EAs), ionization potentials (IPs), molecular electrostatic potentials (MEP), and frontier molecular orbitals (FMOs) have been evaluated. Furthermore their transfer integrals and intrinsic mobilities values have also been calculated. From this study, it is found that hole mobility of octyl containing derivative is raised to 4.69 cm(2) V(-1) s(-1). Moreover with attaching octyl group, hole transfer integral values have also been enhanced in newly designed derivatives. The balanced hole and electron reorganization energies, and improved transfer integrals lead to enhanced mobility in derivatives with octyl group, highlighting them as an efficient hole transfer material. Unlike the other electro-optical properties, the intrinsic hole mobility has increased because of transfer integral values of octyl containing derivative C8-DPNDF due to the dense and close crystal packing of C8-DPNDF. However, photostability of furan-based materials has not changed by increasing length of extended alkyl chain. Thus our present investigation highlights the importance of alkyl auxiliary groups that are often neglected/replaced with simple methyl group to save computation costs. Graphical Abstract The hole and electron reorganization energies of naphtho[2,1-b:6,5-b']difuran derivatives.

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“…3,3,4,4-tetraethoxybut-1-yne (TEB) (1) [8], toward a number of reagents under a variety of conditions. This has eventually led to the synthesis of a range of different products including functionalized allylic and homoallylic alcohols [9,10], highly substituted furans [11,12], amino-substituted furfurals [13], functionalized triazoles [14], deoxygenated carbohydrate analogues [9,[15][16][17], various heterocycles [18][19][20], and functionalized 1,3-dithianes [17,21].…”

mentioning

confidence: 99%