A SIMPLE, ONE-FLASK TRANSFORMATION OF KETONES TO N-METHYL LACTAMS

被引：10
|
作者：
HOFFMAN, RV
SALVADOR, JM
机构：
[1] Department of Chemistry New Mexico State University Las Cruces
来源：
TETRAHEDRON LETTERS | 1991年 / 32卷 / 22期
基金：
美国国家科学基金会;
关键词：
D O I：
10.1016/S0040-4039(00)74345-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-flask conversion of cyclic ketones to N-methyl lactams is described. Reaction of the ketone with triethylorthoformate generates an acetal which is reacted in situ with N-(((p-nitrobenzene)sulfonyl)oxy methylamine 2a(CH3NH-OSO2C6H4NO2). Dealkylation of the resulting O-ethyl imidate with sodium iodide gives the lactam. A variety of lactams, including macrocyclic lactams, are produced simply and in good yields.
引用
收藏
页码：2429 / 2432
页数：4
相关论文
共 50 条
  • [31] A SIMPLE ONE-STEP SYNTHESIS OF STEROIDAL LACTAMS FROM KETONES OF SPIROSTANE AND CHOLESTAN SERIES
    SIDDIQUI, AHU
    RAMESH, D
    RAO, NS
    RAMAIAH, TS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1988, 27 (01): : 61 - 62
  • [32] Simple methods for the labelling of N-methyl amines using isotopically labelled methyl iodide.
    Fellows, I
    Carr, RM
    deBoeck, N
    Montgomery, S
    Waterhouse, I
    Sutherland, DR
    SYNTHESIS AND APPLICATIONS OF ISOTOPICALLY LABELLED COMPOUNDS 1997, 1998, : 507 - 511
  • [33] Influence of the Solvent Content on the Phase Transformation of Sulfadiazine N-Methyl Pyrrolidone Solvate
    Macaringue, Estevao G. J.
    Wu, Songgu
    Liu, Shiyuan
    Xu, Shijie
    Gong, Junbo
    CHEMICAL ENGINEERING & TECHNOLOGY, 2019, 42 (07) : 1435 - 1445
  • [34] ONE-FLASK PREPARATIONS OF 3,3-DIALKOXYBICYCLO[2.2.2]OCT-5-EN-2-ONE DERIVATIVES FROM METHYL VANILLATE, METHYL ISOVANILLATE, AND 2-METHOXY-4-METHYLPHENOL
    CHU, CS
    LEE, TH
    LIAO, CC
    SYNLETT, 1994, (08) : 635 - 636
  • [35] THE RESONANCE EFFECT OF AMIDE GROUP ON THE POLYMERIZABILITY OF LACTAM DERIVATIVES .1. THE INFRARED SPECTRUM OF N-METHYL LACTAMS
    OGATA, N
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1961, 34 (02) : 245 - 248
  • [36] THERMODYNAMIC STUDY OF 1-1 COMPLEX FORMATION BETWEEN N-METHYL LACTAMS + PHENOL IN CARBON TETRACHLORIDE
    SCHMULBACH, CD
    HART, DM
    JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (10): : 3122 - &
  • [37] Simple synthesis of N-methyl aniline over modified kaolin for octane number improvement
    Ma, Hongzhu
    Zhu, Zhigang
    Wang, Bo
    ENERGY & FUELS, 2008, 22 (04) : 2157 - 2159
  • [38] Examination of diverse acid catalysts for use in two-step, one-flask syntheses of porphyrin, n-confused porphyrin, and sapphyrin.
    Geier, GR
    Haynes, DM
    Lindsey, JS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U160 - U160
  • [39] SIMPLE METHOD FOR LABELING PHOSPHATIDYL-N,N-DIMETHYL ETHANOLAMINE AND PHOSPHATIDYL CHOLINE IN N-METHYL MOIETY
    LEKIM, D
    BETZING, H
    ZEITSCHRIFT FUR KLINISCHE CHEMIE UND KLINISCHE BIOCHEMIE, 1974, 12 (05): : 267 - 268
  • [40] A domino type one-flask synthesis of 1-substituted-5-aminoimidazole-4-carboxamides and ring transformation to pyrazine under microwave through suitable aminoimidazoliumcarboxamide
    Chattopadhyay, G
    Saha, TK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2005, 44 (04): : 827 - 830
12345