Reduction of nitro groups by ynamines; synthesis and x-ray crystal structure of n,n-diethyl-3,3a-dihydro-3-methylbenzofuro[3,2-c]isoxazole-3-carboxamide

WIT, A. D. DE; TROMPENAARS, W. P.; Reinhoudt, David N.; Harkema, Sybolt; Hummel, G.J. van

doi:10.1016/s0040-4039(00)77836-1

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Cited by 8 publications

(3 citation statements)

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“…Allyl Chloride (5). Phenyl (bromodichloromethyl)mercury (Seyferth's Reagent) (1.59 g, 3.41 mmol) was suspended in a solution of the ester 3 (400 mg, 2.22 mmol) in benzene (15 mL).…”

Section: Experimental Section11mentioning

confidence: 99%

“…Similarly, this mixture afforded only 5 and 6 (1:3) when heated neat for 1 h at 90 °C. Under these conditions 5 was stable.…”

mentioning

confidence: 98%

“…In addition the distance between 0(1) and H(6) (2.81 A now) would decrease, too. These short distances would cause strong repulsions and distortions of bonds and apparently increase the energy of the "trans" isomer in such a way that it converts into the stable one (5).…”

mentioning

confidence: 99%

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Unusual regioselectivity of dichlorocarbene addition to a norbornene derivative. X-ray structure of the stable product

Schomburg¹,

Landry²

1981

J. Org. Chem.

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“…Allyl Chloride (5). Phenyl (bromodichloromethyl)mercury (Seyferth's Reagent) (1.59 g, 3.41 mmol) was suspended in a solution of the ester 3 (400 mg, 2.22 mmol) in benzene (15 mL).…”

Section: Experimental Section11mentioning

confidence: 99%

“…Similarly, this mixture afforded only 5 and 6 (1:3) when heated neat for 1 h at 90 °C. Under these conditions 5 was stable.…”

mentioning

confidence: 98%

See 1 more Smart Citation

Unusual regioselectivity of dichlorocarbene addition to a norbornene derivative. X-ray structure of the stable product

Schomburg¹,

Landry²

1981

J. Org. Chem.

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Partially Saturated Polynuclear Isoxazoles

Gandolfig¹,

Grünanger²

1999

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions

et al. 2022

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Acylation of nitroalkylmalonates was found to yield substituted isoxazoline derivatives. This redox‐neutral transformation has a wide substrate scope and produces target products with yields up to 92%. Various substituents (aryl, alkyl, and ester) at the C3 and C4 positions of the resulting isoxazolines were also tolerated. A quick assembly of the isoxazoline ring starting from nitroalkenes and malonates was successfully developed. Control experiments showed that the intramolecular ring closure is the most likely key mechanistic step. Subsequent transformations into pyrrolidine and furane derivatives demonstrated the synthetic utility of the obtained products.

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Reduction of nitro groups by ynamines; synthesis and x-ray crystal structure of n,n-diethyl-3,3a-dihydro-3-methylbenzofuro[3,2-c]isoxazole-3-carboxamide

Abstract: Abstract:3-NitrobenzoCblfuran

Cited by 8 publications

References 5 publications

Unusual regioselectivity of dichlorocarbene addition to a norbornene derivative. X-ray structure of the stable product

Unusual regioselectivity of dichlorocarbene addition to a norbornene derivative. X-ray structure of the stable product

Partially Saturated Polynuclear Isoxazoles

Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions

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