Copper‐Catalyzed Aerobic Oxidative Cyclization of Hydrazones to Pyrazolidinones

Santos, A. Dos; Kaı̈m, Laurent El; Grimaud, Laurence; Ronsseray, Caroline

doi:10.1002/ejoc.201100261

Cited by 5 publications

(3 citation statements)

References 49 publications

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“…1125 Treatment of hydrazono amides to oxidative conditions resulted in a cycloaddition and subsequent oxidation, giving the pyrazolidinone products in moderate to good yield (Scheme 591). The amide nitrogen can support either allyl or methyl groups, while the hydrazone aryl is limited to ortho -xylenyl and para -chloro phenyl rings.…”

Section: Reactions Of Aminesmentioning

confidence: 99%

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Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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24 peroxide [Cu I (pyr)(tpb)] 10 mol % TBHP, 1 atm O 2 , 1:2 AcOH/pyr, rt, 24 h ∼2.5 26 74 g 35 25 n-hexane aldehyde CuCl 2 , 18-crown-6 1 atm O 2 , MeCHO, CH 2 Cl 2 , 70 °C, 24 h 2.4 91 h 9 34a 26 n-decane aldehyde Cu II Cl 16 Pc-AM(PS) 3 equiv of PhCHO, MeCN, 1 atm O 2 , 50 °C 15.4 100 i 61 a See Chart 2 for ligand structures. b Also 28% cyclohexene. c Also 26% cyclohexene. d Mixture of alcohol and hydroperoxide. e Remainder of product is cyclohexene. f Approximately 93:7 of 1-adamantol/2-adamantol. g Approximately 98:2 of 1-adamantol/2-adamantol. h Afforded oxidation products in an approximately 1:1 ratio at the 2-and 3-positions. i Mixture of decanones.

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Section: Reactions Of Aminesmentioning

confidence: 99%

“…Grimaud and co-workers reported a tandem cyclization–oxidation of hydrazones to pyrazolidinones . Treatment of hydrazono amides to oxidative conditions resulted in a cycloaddition and subsequent oxidation, giving the pyrazolidinone products in moderate to good yield (Scheme ).…”

Section: Reactions Of Aminesmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

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“…We recently reported a new synthesis of fused pyrazolidinone under oxidative conditions from simple hydrazone derivatives ( Scheme 1 ) [ 13 ]. The cascade features a [3 + 2] cycloaddition coupled with an aerobic oxidation of the resulting pyrazolidine.…”

Section: Introductionmentioning

confidence: 99%

Ugi post-condensation copper-triggered oxidative cascade towards pyrazoles

Santos¹,

Kaim²,

Grimaud³

et al. 2011

Beilstein J. Org. Chem.

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ChemInform Abstract: Copper‐Catalyzed Aerobic Oxidative Cyclization of Hydrazones to Pyrazolidinones.

Santos¹,

Kaı̈m²,

Grimaud³

et al. 2011

ChemInform

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Copper-Catalyzed Aerobic Oxidative Cyclization of Hydrazones to Pyrazolidinones. -Cascade [3 + 2]-cycloaddition/oxidation reactions of N-aryl hydrazones lead to the various bicyclic pyrazolidinones with moderate to good yields. Aryl substituents at the diazo group is essential. The authors suggest that the amount of air in the reaction system despite working under routine argon conditions is sufficient for oxidation. The reaction carried out on air is difficult to control. Under prolonged heating of (Ia) a complex cascade of multiple oxidation and cyclization steps leads to a tetracyclic product (III). -(DOS SANTOS, A.; EL KAIM, L.; GRIMAUD*, L.; RONSSERAY, C.; Eur. J. Org. Chem. 2011, 17, 3117-3121, http://dx.

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Copper‐Catalyzed Aerobic Oxidative Cyclization of Hydrazones to Pyrazolidinones

Abstract: N‐Aryl hydrazones participate, under copper catalysis, in a [3+2] cycloaddition/aerobic oxidation cascade reaction to form pyrazolidinones. The starting hydrazones were prepared by three‐component coupling of allylic amines, acyl chlorides, and aryl diazonium salts.

Cited by 5 publications

References 49 publications

Aerobic Copper-Catalyzed Organic Reactions

Aerobic Copper-Catalyzed Organic Reactions

Ugi post-condensation copper-triggered oxidative cascade towards pyrazoles

ChemInform Abstract: Copper‐Catalyzed Aerobic Oxidative Cyclization of Hydrazones to Pyrazolidinones.

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