Synthesis of carbonyl and dicarbonyl compounds from organometallic reagents and N-imidazolium-N-methyl amides and bis-amides

被引:5
|
作者
delasHeras, MA [1 ]
Vaquero, JJ [1 ]
Navio, JLG [1 ]
AlvarezBuilla, J [1 ]
机构
[1] UNIV ALCALA DE HENARES, DEPT QUIM ORGAN, E-28871 ALCALA DE HENARES, MADRID, SPAIN
关键词
D O I
10.1016/0040-4020(96)00882-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of selective acylating agents is described from the reaction of carboxylic acids with 3-methyl-1-methylamino-3H-imidazol-1-ium salts in the presence of appropriate coupling reagents. The amides and bis-amides thus prepared reacted selectively with organometallics to afford ketones and diketones and with DIBALH to give aldehydes and dialdehydes in high yields. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:14297 / 14310
页数:14
相关论文
共 50 条
  • [41] SYNTHESIS AND CARCINOSTATIC ACTION OF N-[BIS(2-CHLOROETHYL)-AMINOMETHYL]-AMIDES
    SCHONENBERGER, H
    BINDL, L
    ADAM, A
    ARCHIV DER PHARMAZIE, 1973, 306 (01) : 64 - 75
  • [42] SYNTHESIS OF NEW N,N-BIS[2-(ARYLTHIO)ETHYL]AMIDES AND N,N-BIS[2-(ARYLTHIO)ETHYL]AMINES
    KASZUBSK.J
    BAL, S
    ROCZNIKI CHEMII, 1974, 48 (02): : 325 - 328
  • [43] APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESES .1. REACTIONS OF THE N,N-DIALKYLPYRIDYLCARBOXYLIC AMIDES WITH LITHIUM AMIDES - REGIOSELECTIVE LITHIATION OF N,N-DIISOPROPYLPYRIDYLCARBOXYLIC AMIDES, A USEFUL METHOD FOR SYNTHESIS OF 2,3- AND 3,4-DISUBSTITUTED PYRIDINES
    EPSZTAJN, J
    BERSKI, Z
    BRZEZINSKI, JZ
    JOZWIAK, A
    TETRAHEDRON LETTERS, 1980, 21 (49) : 4739 - 4742
  • [44] GENERATION OF N-ACYL IMINIUM IONS FROM IONIZATION REACTIONS OF N-TRIFLYLOXY AMIDES - A NEW METHOD FOR THE SYNTHESIS OF N-ISOPROPOXYALKYL AMIDES
    HOFFMAN, RV
    NAYYAR, NK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 377 - ORGN
  • [45] Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic control vs. kinetic control of N,N-Boc2-amides
    Li, Guangchen
    Szostak, Michal
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (20) : 3827 - 3831
  • [46] N,N-Bis-(dimethylfluorosilylmethyl)amides of N-organosulfonylproline and sarcosine: synthesis, structure, stereodynamic behaviour and in silico studies
    Nikolin, Alexey A.
    Kramarova, Eugenia P.
    Shipov, Alexander G.
    Baukov, Yuri I.
    Negrebetsky, Vadim V.
    Arkhipov, Dmitry E.
    Korlyukov, Alexander A.
    Lagunin, Alexey A.
    Bylikin, Sergey Yu.
    Bassindale, Alan R.
    Taylore, Peter G.
    RSC ADVANCES, 2016, 6 (79): : 75315 - 75327
  • [47] SYNTHESIS OF S, N-KETENACETALS FROM BETA-DICARBONYL COMPOUNDS AND METHYL THIOCYANATE
    DOROKHOV, VA
    GORDEEV, MF
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1988, 37 (04): : 820 - 821
  • [48] SYNTHESIS OF ALPHA-AZIDO AND ALPHA-AMINO AMIDES FROM N-[(METHYLSULFONYL)OXY] AMIDES
    HOFFMAN, RV
    NAYYAR, NK
    CHEN, WT
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09): : 2355 - 2359
  • [49] Synthesis and Conformational Analysis of N-Azulenyl-N-methyl Amides: Influence of Coplanarity on Amide Conformational Preference
    Ito, Ai
    Tsuchida, Ai
    Arakawa, Mari
    Yunoki, Masayuki
    Tomita, Mayuko
    Ishii, Ayako
    Yamasaki, Ryu
    Okamoto, Iwao
    ACS OMEGA, 2025, 10 (12): : 12590 - 12602
  • [50] N-METHYL-N-TRIMETHYLSILYL-TRIFLUOROACETAMIDE A NEW SILYLATING AGENT FROM SERIES OF SILYLATED AMIDES
    DONIKE, M
    JOURNAL OF CHROMATOGRAPHY, 1969, 42 (01): : 103 - &