Synthesis and ring opening reactions of 2-glyco-1,4-dimethyl-3-nitro-7-oxabicyclo[2.2.1]hept-5-enes

Araújo, Noelia; Gil, M. Cuesta; Román, Emilio; Serrano, José Antonio

doi:10.1016/j.tet.2010.02.027

Cited by 3 publications

(3 citation statements)

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“…Likewise, nitrodienes 286 – 288 (Figure ) have been proposed as intermediates in similar mechanisms. The formation of cyclohexadienes from 7-oxabicyclo[2.2.1]heptenes bearing electron-withdrawing substituents was described by Brion, who reported a highly stereoselective synthesis (51–85% yields) of cyclohexadienol 290 and cyclohexenol systems by a base-induced β-elimination of the heteroatom bridge of substituted 7-oxabicyclo[2.2.1]heptenes 289 and heptanes (Scheme ).…”

Section: -Nitro-13-dienesmentioning

confidence: 95%

“…Functionalized 1,4-dihydronaphthalenes have been obtained through an inverse electron-demand aryne Diels−Alder reaction with acyclic dienes bearing electron-withdrawing substituents. 62 Thus, 75% 1-nitro-4-phenyl-1,4-dihydronaphthalene (113) (apparently unstable to flash chromatography on silica gel) was obtained from 1-nitro-4-phenylbuta-1,3-diene (111) and benzyne, generated from 2-(trimethylsilyl)phenyl triflate (112) and CsF in acetonitrile (Scheme 28).…”

Section: Introductionmentioning

confidence: 99%

“…111 A case similar to that presented in Scheme 69, where intramolecular nucleophilic attacks from hydroxyl groups on a nitrodiene system were proposed, was observed during a study into Diels−Alder reactions between sugar-derived nitroalkenes with 2,5-dimethylfuran under high pressure; here, the presence of intermediate 1-nitro-1,3-nitrodienes 282 in the reaction mixture supported mechanisms leading to bicyclic and tricyclic oxygenated heterocycles 283−285 (Scheme 73). 112 Likewise, nitrodienes 286−288 (Figure 5) have been proposed as intermediates 113 1-Nitro-1,3-dienes have also been proposed as intermediates in the preparation of substituted phenols from 2-alkylated 1,3dinitropropanes. 115 Thus, proceeding by a one-pot tandem Michael nitroaldol reaction with acrolein 183, compounds 291 formed a diastereoisomeric mixture of the cyclohexanols 292 (68−88% yields) which, after treatment with potassium carbonate followed by acidic workup, led to nitrocyclohexenones 293.…”

Section: Introductionmentioning

confidence: 99%

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Conjugated Nitrodienes. Synthesis and Reactivity

et al. 2013

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Section: -Nitro-13-dienesmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Conjugated Nitrodienes. Synthesis and Reactivity

et al. 2013

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A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-γ-aminated nitroalkenes derived from L-α-amino acids

Pereira

Moura²,

Vieira³

et al. 2013

Beilstein J. Org. Chem.

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SummaryNew chiral (S,E)-γ-N,N-dibenzylated nitroalkenes 2a–c were synthesized from natural L-(α)-amino acids in five steps with overall yields of 68–88%. The conjugate addition of hydride, methoxide, nitronate and azide nucleophiles to 2a–c led to the corresponding chiral 1,3-nitroamines in 74–90% yield. The conjugate addition of cyanide anion to 2a,b was followed by HNO2 elimination affording chiral aminated acrylonitriles (73–98%). On the other hand, the azide anion reacted with 2a, in acetonitrile, via a [3 + 2]-cycloaddition in which HNO2 was lost, providing the corresponding 1,2,3-triazole derivative. Direct reduction of 1,3-nitroamine derivatives 9a,b produced the corresponding 1,3-diamines in good yields.

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Synthesis and Reaction of Novel Spiro Pyrazol-3-ones Containing Oxirane Moiety

Maruoka¹,

Nagabuchi²,

Masumoto³

et al. 2021

HETEROCYCLES

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An efficient synthesis and reaction of a series of spiro pyrazol-3-one derivatives containing oxirane moiety are described. The convenient substrates, three types of pyrazole-4,5-diones, were reacted with phenacyl bromides in the presence of triethylamine in ethanol at room temperature to give the corresponding spiro epoxide-pyrazol-3-ones in moderate to good yields. Furthermore, thermal treatment of spiro compounds with pyrrolidine in the presence of water caused ring transformation easily to afford the corresponding pyridazinone derivatives. These methods provide several advantages such as operational simplicity, shorter reaction time, and higher yields. All the synthesized compounds were characterized by spectroscopic analysis.

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Synthesis and ring opening reactions of 2-glyco-1,4-dimethyl-3-nitro-7-oxabicyclo[2.2.1]hept-5-enes

Cited by 3 publications

References 48 publications

Conjugated Nitrodienes. Synthesis and Reactivity

Conjugated Nitrodienes. Synthesis and Reactivity

A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-γ-aminated nitroalkenes derived from L-α-amino acids

Synthesis and Reaction of Novel Spiro Pyrazol-3-ones Containing Oxirane Moiety

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