Intramolecular cycloaddition of fluorinated 1,3,4-oxadiazoles to dienes

Vasil'ev, N. V.; Romanov, D. V.; Bazhenov, A. A.; Zatonsky, George V.

doi:10.1016/j.jfluchem.2007.02.020

Cited by 19 publications

(10 citation statements)

References 11 publications

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“…1 H NMR (CDCl 3 ): δ = 1.80-1.92 and 2.01-2.35 (m, 9H, CH 2 of cyclopentane and NH); 2.39 (s, 3H, CH 3 ); 3.70 (s, 2H, CH 2 of Benzyl group); 6.06 and 6.28 (s, 2H, CH-furyl); 7.26-7.44 (m, 7H, CH-Ar and Vinyl). 13 …”

Section: N-(2-furylmethyl)-n-(1-{5-[(e)-1-methyl-2-phenyl-1-ethenyl]-mentioning

confidence: 99%

“…11 In 1990, it was found that 2-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD) functioned as an excellent electron transport material (ETM) in an organic multilayer EL diode. 12 1,3,4-Oxadiazoles are also very important starting materials for cycloaddition reactions, 13 in the synthesis of furans and natural products (Figure 1). 14 The aza-Wittig reactions of iminophosphoranes have attracted much attention because of their usefulness in the synthesis of nitrogen-containing heterocyclic compounds since they were first prepared in 1919 by Staudinger and Meyer.…”

Section: Introductionmentioning

confidence: 99%

“…cyclopentane and NH); 3.64 (s, 2H, CH 2 of Benzyl group); 7.01 (d, 1H, 3 J HH = 16.5 Hz, CH Vinyl); 7.12-7.55 (m, 11H, CH-Ar and Vinyl) 13. C NMR (CDCl 3 ): δ = 23.Benzyl-N-(1-{5-[(E)-2-(4-chlorophenyl)-1-ethenyl]-1,3,4-oxadiazol-2-yl]cyclopentyl}amine (5h) Yellow Oil (yield 82%), IR (neat) (ν max /cm −1 ): 3440 (NH), 2964 (C H), 1645 (C N), 1488 (C C, aromatic), 719 (C Cl).…”

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confidence: 99%

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The Reaction of N-Isocyaniminotriphenylphosphorane with Cyclopentanone and A Primary Amine in the Presence of An E-Cinnamic Acid Derivative

Ahankar

Ramazani

Ahmadi

2014

Phosphorus, Sulfur, and Silicon and the Related Elements

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Section: N-(2-furylmethyl)-n-(1-{5-[(e)-1-methyl-2-phenyl-1-ethenyl]-mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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The Reaction of N-Isocyaniminotriphenylphosphorane with Cyclopentanone and A Primary Amine in the Presence of An E-Cinnamic Acid Derivative

Ahankar

Ramazani

Ahmadi

2014

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…It is evident that larger separation between two -bonds in the diene favors the formation of cage adduct, such in the case of diallyl ether, where reaction rapidly proceeds at 130 o C to give 132 [38]. The reaction of OD with divinyl sulfide occurred only at high temperature, leading to almost identical amounts of cyclic products 125 and 126, arising from inter and intramolecular reactions respectively.…”

Section: Intramolecular [4+2]/[3+2] Cycloaddition Reactionsmentioning

confidence: 99%

Tandem [4+2]/[3+2] Cycloadditions of 1,3,4-Oxadiazoles with Alkenes

Margetić¹,

Trošelj²,

Johnston

2011

MROC

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A review on the tandem [4+2]/[3+2] cycloaddition reactions of 1,3,4-oxadiazoles with alkenes is presented. This reaction presents a powerful synthetic tool in the construction of complex polycyclic molecules in a one-pot reaction. Special attention is paid to synthesis of [n]polynorbornane and oxanorbornyl systems. In continuation, a review on the 1,3,4-oxadiazole reactions used in stereoselective total synthesis of alkaloids is given. Both intermolecular and intramolecular tandem [4+2]/[3+2] reactions are discussed. Stereospecificities and mechanistic rationale of various reactions are supported by quantum-chemical calculations (RHF/6-31G*). TANDEM [4+2]/[3+2] CYCLOADDITION REACTIONS OF OXADIAZOLES WITH ACYCLIC ALKENESVasil'ev reported that a series of polyfluorinated 1,3,4oxadiazoles 1-4 undergo a tandem [4+2]/[3+2] cycloadditions with acyclic alkenes, representative examples are given in Scheme 3.[15] Ethylene reacts in a sealed vessel at 200-220 o C with OD producing 1,4-bis(trifluoromethyl)-7-oxabicyclo[2.2.1]heptane 5 in 41% yield. Stereochemical or regiochemical factors come into play when the alkene bears substituents. Both regio-isomers (2,5-, 2,6-) and stereo-isomers (exo-, endo-) are then possible. The regiochemical outcome depends on the size of the substituent rather than its electronic properties. Thus, the reaction of propylene, ethyl vinyl ether, ethyl acrylate, methyl metacrylate, and isoprene give mixtures of the 2,5-and the 2,6-isomers 9-13 in each case, whereas reaction with styrene regiospecifically gave product 14. TANDEM [4+2]/[3+2] CYCLOADDITION REACTIONS OF OXADIAZOLES WITH CYCLIC ALKENESA range of cycloalkenes have been found to react with OD to form highly symmetrical coupled products 15 (n=1,2,3,5), in which the rings were exo-fused to the 7-oxanorbornane subframe (Scheme 4) [18].Reaction with cyclopentadiene proceeds in relatively mild conditions, while cyclopentene, cyclohexene and 1,4-cyclohexadiene require more drastic conditions, heating at 140-200 o C (Scheme 5) N N

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“…1-8 1,3,4-Oxadiazoles are also important starting materials for cycloaddition reactions 9 in the synthesis of furans and natural products. 10 1,3,4-Oxadiazoles were recently tested for their possible use in organic light-emitting diodes (OLED).…”

Section: Introductionmentioning

confidence: 99%