Synthesis of 1-aryl-2-propanones

LI Li1, LIU Zhanpeng2, LIN Yuanbin2

PDF(156 KB)
PDF(156 KB)
Front. Chem. China ›› 2008, Vol. 3 ›› Issue (3) : 338-343. DOI: 10.1007/s11458-008-0047-7

Synthesis of 1-aryl-2-propanones

  • LI Li1, LIU Zhanpeng2, LIN Yuanbin2
Author information +
History +

Abstract

A new convenient synthesis of a series of 1-aryl-2-propanones using aromatic amines as precursors, via diazo-reaction and improved Meerwein arylation reaction under mild conditions, was achieved. In addition, 1-[3,5-bis(trifluoromethyl)phenyl]-2-propanone is a new compound among the synthesized compounds. This approach is an efficient synthetic method for the aryl-propanones with different substituting groups.

Cite this article

Download citation ▾
LI Li, LIU Zhanpeng, LIN Yuanbin. Synthesis of 1-aryl-2-propanones. Front. Chem. China, 2008, 3(3): 338‒343 https://doi.org/10.1007/s11458-008-0047-7

References

1. Klapas A Campos K R Chen C Y Volante R P Preparationof enamides via palladium- catalyzedamidation of enol tosylates.Org Lett 2005 7(6)11851188. doi:10.1021/ol050117y
2. Pan Z L Liu X Y Liang Y M A new useful entry of IBX: the synthesis and structureof α-(2-iodobenzoyloxy)ketonesTetrahedronLett 2004 45(14)41014104. doi:10.1016/j.tetlet.2004.03.158
3. Gangjee A Yang J Ihnat M A Kamat S Antiangiogenicand antitumor agents: design, synthesis, and evaluation of novel 2-amino-4-(3-bromoanilino)-6-benzylsubstitutedpyrrolo[2,3-d] pyramiddines as inhibitors of receptor tyrosine kinasesBioorg & Med Chem 2003 11(23)51555170. doi:10.1016/j.bmc.2003.08.034
4. Come J H Green J Marhefka C Harbeson S L Pham L Aminofurazan compounds useful as proteinkinase inhibitorsUS 0148640, 2005 [ChemAbstr 2004, 142, 280214]
5. Poindextre G S Luo G L Chen L Alpha-aminoamide derivatives as melanocortin agonistsUS 0232807, 2003 [Chem Abstr 2004, 140, 42460]
6. Muto S Itai A AntiallergicE P1514544, 2003 [Chem Abstr 2004, 140, 42216]
7. Muto S Itai A Therapeutic drug for diabetesWO 2003103658, 2003 [Chem Abstr 2004, 140, 42204]
8. Romero A G Darlington W H Therapeutically useful 2-aminotetralinderivativesUS 6331636, 2001 [Chem Abstr 2002, 136, 37413]
9. Micale N Zappala M Grasso S Synthesis and antitumor activity of 1,3-benzodioxole derivativesFarmaco 2002 57(10)853859. doi:10.1016/S0014‐827X(02)01276‐4
10. Erdely B Szabo A Birincsik L Hoschke A Process developmentof methylenedioxyphenylacetone chiral bioreductionJ Mol Catal B: Enzym 2004 29(2)195199. doi:10.1016/j.molcatb.2003.10.015
11. Nunno D L Vitale P Scilimati A Tacconelli S Patrignani P Novel synthesis of 3,4-diarylisoxazoleanalogues of valdecoxid: reversal cyclooxygenase-2 selectivity bysulphonamide group removalJ Med Chem 2004 47(20)48814890. doi:10.1021/jm040782x
12. Fraaije M W Kamerbeek N M Heidekamp A J Fortin R Janssen D B The prodrug activator etaa from mycobacteriumtuberculosis is a baeyer-villiger monooxygenaseJ Biol Chem 2004 279(5)33543360. doi:10.1074/jbc.M307770200
13. Gangjee A Yang J Ihnat M A Kamat S Antiangiogenicand antitumor agents: design, synthesis, and evaluation of novel 2-amino-4-(3-bromoanilino)-6-benzylsubstitutedpyrrolo[2,3-d] pyramiddines as inhibitors of receptor tyrosine kinasesBioorg & Med Chem 2003 11(23)51555170. doi:10.1016/j.bmc.2003.08.034
14. Justik M W Koser G F Oxidative rearrangements ofarylalkenes with [hydroxyl(tosy- loxy)iodo]benzene in 95% methanol:a general, regiospecific synthesis of α-aryl ketonesTetrahedron Lett 2004 45(32)61596163. doi:10.1016/j.tetlet.2004.06.029
15. Rebrovic L Koser G F Reaction manifolds of alkeneswith [hydroxyl(tosy-loxy)iodo]benzene: stereospecific syn-1,2-ditosyloxylationof the carbon-carbon double bond and other processesJ Org Chem 1984 49(13)24622472. doi:10.1021/jo00187a032
16. Kozikowski A P Wetter H F Transition metai in organicsynthesisSynthesis 1976 (9)561590. doi:10.1055/s‐1976‐24126
17. Horwell D C Timms G H Streoselectivity in the catalytichydrogenation of an enamine. Selective formation of cis- or trans-tertiaryamines.Synth Commun 1979 9(3)223231. doi:10.1080/00397917908066700
18. Bright Z R Luyeye C R Marie Morton A S Sedenko M Landolt R G Bronzi M J Bohovic K M Hendrickson W H Alex Gonser M W Lapainis T E Competing reactions of secondaryalcohols with sodium hypochlorite promoted by phase-transfer catalysisJ Org Chem 2005 70(2)684687. doi:10.1021/jo0490651
19. Bianchini G Crucianelli M Angelis F D Neri V Saladino R Highly efficient C-H insertion reactionsof hydrogen peroxide catalyzed by homogeneous and heterogeneous methyltrioxorheniumsystems in ionic liquidsTetrahedron Lett 2005 46(21)24272432. doi:10.1016/j.tetlet.2005.02.056
20. Hunsen M Pyridiniumchlorochromate catalyzed oxidation of alcohols to aldehydes and ketoneswith periodic acidTetrahedron Lett, 2005 46(10)16511653. doi:10.1016/j.tetlet.2005.01.076
21. Okabe K Toshiharu Ohta T O Shudo K Novel electrophilic species equivalent to α-keto cations. Reactions of o,o-diprotonated nitro olefins with benzenesyield arylmethyl ketones.J Org Chem 1989 54(4)733734. doi:10.1021/jo00265a001
22. Clay J M Vedejs E Hydroboration with pyridineborane at room temperatureJ Am Chem Soc 2005 127(16)57665767. doi:10.1021/ja043743j
23. Collins S Hong Y Hoover G J Veit J R Additions ofalkyllanthanum triflates to carbonyl compounds: reactive organometallicnucleophilesJ Org Chem 1990 55(11)35653568. doi:10.1021/jo00298a035
24. Raucher S Koolpe G A Synthesis of substituted indolesvia Meerwein arylationJ Org Chem 1983 48(12)20662069. doi:10.1021/jo00160a026
25. Hegedus L S Allen G F Bozell J J Waterman E L Palladium-assistedintramolecular amination of olefins. Synthesis of nitrogen heterocycles.J Am Chem Soc 1978 100(18)58005807. doi:10.1021/ja00486a035
26. Rondestvedt C S Vogl J r O Arylation of unsaturated systemsby free radicals. IV. effects of catalyst, pH and solvent upon theMeerwein reaction.J Am Chem Soc 1955 77(12)34013402. doi:10.1021/ja01617a082
27. Koelsch C F Boekelheide V The coupling of α, β-unsaturatedcompounds with diazonium saltsJ Am ChemSoc 1944 66(3)412415. doi:10.1021/ja01231a031
28. Wang B R OrganicSynthesis ReactionBeijingScience Press 1985 758759(in Chinese)
29. Finger G C Reed F H Finnerty J L Aromatic fluorine compounds. V. 1,3,5-trifluorobenzene.J Am Chem Soc 1951 73(1)153155. doi:10.1021/ja01145a055
30. Luo N Mu Z D Synthesis of N-ethyl-α-methyl-m-(trifluoromethyl)phenethylamineChem Res Appl 1997 9(2)135137(in Chinese)
31. Wojciech Z Beckmannrearrangement of benzylideneacetion oximes and their derivatives.Part III. rearrangement of 3-alkyl-4-aryl-3-butene-2-one oximes.Pol J Chem 1978 52(11)22332236
32. Stefan G Danuta R R Marek L Preparation and properties of substituted benzyl methylketonesPol J Chem 1979 53(4)849852
33. Muller A Meszaros M Magda L S Szara I Dimeric propenylphenol ethers. XIII. on methanethole and its tetralin isomers. J Org Chem 1951 16(7)10031024. doi:10.1021/jo50001a001
34. Sutherland R G Chowdhury R L Piorko A Lee C C Functionalizationof aromatic and heterocyclic systems. Region-selective introductionof 2-oxoalkyl chain or cyano functions via organoiron complexes.J Org Chem 1987 52(20)46184620. doi:10.1021/jo00229a038
35. Jilsdorf R T Nord F F Reverse addition of lithiumaluminium hydride to nitroolefinsJ Am ChemSoc 1952 74(7)18371843. doi:10.1021/ja01127a064
36. Julian P L Oliver J J Methyl benzyl ketone[2-propanone,1-phenyl-] [(A) (from phenyllacetic and acetic acids)] [(B)(from α-phenylacetoacetonitrile)]Org Synth Coll 1943 2389392
PDF(156 KB)

Accesses

Citations

Detail

Sections
Recommended

/