Substitution of Acyl for Acetyl with N‐Acylbenzotriazoles Catalyzed by Samarium Triiodide

References

• Zhang , Y. , Jiao , J. and Flowers , R. A. 2006 . Mild conversion of β‐diketones and β‐ketoesters to carboxylic acids . J. Org. Chem. , 71 ( 12 ) : 4516 – 4520 .
   PubMed Web of Science ®Google Scholar
• Bunlaksananusorn , T. and Rampf , F. 2005 . A facile one‐pot synthesis of chiral β‐amino esters . Synlett , : 2682 – 2684 .
   Google Scholar
• Lou , S. , Taoka , B. M. , Ting , A. and Schaus , S. E. 2005 . Asymmetric Mannich reactions of β‐keto esters with acyl imines catalyzed by cinchona alkaloids . J. Am. Chem. Soc. , 127 ( 32 ) : 11256 – 11257 .
   PubMed Web of Science ®Google Scholar
• Ngo , H. L. , Hu , A. and Lin , W. 2003 . Highly enantioselective catalytic asymmetric hydrogenation of β‐keto esters in room temperature ionic liquids . Chem. Commun. , 9 ( 15 ) : 1912 – 1913 .
   Google Scholar
• Kel'in , A. V. 2003 . Recent advances in the synthesis of 1,3‐diketones . Current. Org. Chem. , 7 ( 16 ) : 1691 – 1171 .
   Web of Science ®Google Scholar
• Benetti , S. and Romagnoli , R. 1995 . Mastering β‐keto esters . Chem. Rev. , 95 ( 4 ) : 1065 – 1114 .
   Web of Science ®Google Scholar
• Viscontini , M. and Merckling , N. 1952 . A new β‐oxo ester synthesis . Helv. Chim. Acta. , 35 : 2280 – 2282 .
   Web of Science ®Google Scholar
• Jung , J.‐C. , Watkins , E. B. and Avery , M. A. 2002 . Synthesis of 3‐substituted and 3,4‐disubstituted pyrazolin‐5‐ones . Tetrahedron , 58 ( 18 ) : 3639 – 3646 .
   Web of Science ®Google Scholar
• Lash , T. D. , Mani , U. N. , Lyons , E. A. , Thientanavanich , P. and Jones , A. 1999 . Normal and abnormal heme biosynthesis, 2.1: Synthesis and metabolism of type‐III pentacarboxylic porphyrinogens: Further experimental evidence for the enzymic clockwise decarboxylation of uroporphyrinogen‐III . J. Org. Chem. , 64 ( 2 ) : 478 – 487 .
   Web of Science ®Google Scholar
• Rathke , M. W. and Cowan , P. J. 1985 . Procedures for the acylation of diethyl malonate and ethyl acetoacetate with acid chlorides using tertiary amine bases and magnesium chloride . J. Org. Chem. , 50 ( 15 ) : 2622 – 2624 .
   Web of Science ®Google Scholar
• Hao , W. , Zhang , Y. , Ying , T. and Lu , P. 1996 . A facile route to convert acetylacetone into other β‐diketones with acyl chlorides promoted by samarium triiodide . Synth. Commun. , 26 ( 12 ) : 2421 – 2427 .
   Web of Science ®Google Scholar
• Renault , O. , Guillon , J. , Dallemagne , P. and Rault , S. 2000 . Efficient synthesis of 2‐aryl‐6‐methyl‐2,3‐dihydro‐1H‐pyridin‐4‐ones . Tetrahedron Lett. , 41 ( 5 ) : 681 – 683 .
   Web of Science ®Google Scholar
• Zhang , Y. D. and Zhang , Y. M. 2004 . Trace amount of metallic samarium catalysed aroyl substitution reactions of a β‐keto ester in air . J. Chem. Res., Synop. , 7 : 510 – 512 .
   Google Scholar
• Gukhman , E. V. and Reutov , V. A. 1999 . Boron difluoride β‐diketonates, II: Synthesis of boron difluoride naphthoyl‐ and anisoylbenzoylmethanates substituted in the benzene ring . Russ. J. Gen. Chem. , 69 ( 10 ) : 1608 – 1611 .
   Web of Science ®Google Scholar
• March , J. 1985 . March's Advanced Organic Chemistry , 3rd edn. 436 – 436 . New York : John Wiley & Sons .
   Google Scholar
• Taylor , E. C. , Hawks , G. H. III and McKillop , A. 1968 . Thallium in organic synthesis, I: Alkylation and acylation of beta‐dicarbonyl compounds . J. Am. Chem. Soc. , 90 ( 9 ) : 2421 – 2422 .
   Google Scholar
• McElvain , S. M. and Weber , K. H. 1941 . Acyl exchanges between esters and 1,3‐diketones and β‐keto esters . J. Am. Chem. Soc. , 63 ( 8 ) : 2192 – 2197 .
   Google Scholar
• Singh , B. and Lesher , G. Y. 1978 . Convenient preparations of ethyl 3‐oxopentanoate and 3,5‐disubstituted 1,2‐oxazole‐4‐carboxylic acids from a common type of intermediate . Synthesis , 11 : 829 – 830 .
   Google Scholar
• Elmorsy , S. S. , Badawy , D. S. and Khatab , T. K. 2005 . Evaluation of TCS/ZnCl2 with acetic anhydride as an acetylating reagent for methylene ketones . Phosphorus, Sulfur Silicon , 180 ( 1 ) : 109 – 116 .
   Web of Science ®Google Scholar
• Katritzky , A. R. , Wang , Z. , Wang , M. , Wilkerson , C. R. , Hall , C. D. and Akhmedov , N. G. 2004 . Preparation of β‐keto esters and β‐diketones by C‐acylation/deacetylation of acetoacetic esters and acetonyl ketones with 1‐acylbenzotriazoles . J. Org. Chem. , 69 ( 20 ) : 6617 – 6622 .
   PubMed Web of Science ®Google Scholar
• Katritzky , A. R. , Suzuki , K. and Wang , Z. 2005 . Acylbenzotriazoles as advantageous N‐, C‐, S‐, and O‐acylating agents . Synlett , 11 : 1656 – 1665 .
   Google Scholar
• Buckingham , J. 1982 . Dictionary of Organic Compounds , 5th edn. New York : Chapman and Hall .
   Google Scholar
• Doleschall , G. A. 1988 . New enamine‐salt for the synthesis of γ‐alkylated ethyl acetoacetate derivatives . Tetrahedron Lett. , 29 ( 48 ) : 6339 – 6340 .
   Web of Science ®Google Scholar
• Houghton , R. P. and Lapham , D. J. 1982 . A modified preparation of β‐keto esters . Synthesis , 6 : 451 – 453 .
   Google Scholar
• Ratovelomanana‐Vidal , V. , Girard , C. , Touati , R. , Tranchier , J. P. , Ben Hassine , B. and Genet , J. P. 2003 . Enantioselective hydrogenation of β‐keto esters using chiral diphosphine‐ruthenium complexes: Optimization for academic and industrial purposes and synthetic applications . Adv. Synth. Catal. , 345 ( 1–2 ) : 261 – 274 .
   Web of Science ®Google Scholar
• Walker , H. G. , Sanderson , J. J. Jr. and Hauser , C. R. 1953 . Acetoacetylation of aromatic compounds by boron fluoride to form β‐diketones:Failure with boron and aluminum chlorides . J. Am. Chem. Soc. , 75 ( 16 ) : 4109 – 4110 .
   Google Scholar