A NEW APPROACH TO THE SYNTHESIS OF 2-AZA-1,3-DIENES THROUGH A NOVEL 1,4-REARRANGEMENT OF A TRIMETHYLSILYL GROUP FROM NITROGEN TO CARBON

被引：0
|
作者：
DEGL'INNOCENTI, A
MORDINI, A
PINZANI, D
REGINATO, G
RICCI, A
机构：
[1] DIPARTIMENTO CHIM ORGAN U SCHIFF, CNR, CTR COMPOSTI ETEROCICLICI, VIA G CAPPONI 9, I-50121 FLORENCE, ITALY
[2] DIPARTIMENTO CHIM ORGAN A MANGINI, I-40136 BOLOGNA, ITALY
来源：
SYNLETT | 1991年 / 10期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The metalation of N,N,3-tris(trimethylsilyl)-2-propen-1-amine (1) with the equimolar mixture butyllithium/diisopropylamine/potassium tert-butoxide, followed by quenching with aldehydes or ketones, leads to substituted 2-aza-1,3-dienes (N-alkylidene-3,3-bis(trimethylsilyl)-1-propen-1-amines) in satisfactory yield through a novel N --> C 1,4-rearrangement of a trimethylsilyl group.
引用
收藏
页码：712 / 714
页数：3
相关论文
共 50 条
  • [1] 2-AZA-1,3-DIENES .1. SYNTHESIS AND STRUCTURE OF 4-AMINO-2-AZA-1,3-DIENES
    SCHOENI, JP
    FLEURY, JP
    TETRAHEDRON, 1975, 31 (07) : 671 - 678
  • [2] 2-AZA-1,3-DIENES - A NEW APPROACH TO SUBSTITUTED 2-AMINOPYRAZINES
    LANG, M
    SCHOENI, JP
    PONT, C
    FLEURY, JP
    HELVETICA CHIMICA ACTA, 1986, 69 (04) : 793 - 802
  • [3] 2-AZA-1,3-DIENES - SYNTHESIS AND PROPERTIES OF 1-ALKYLPYRAZONE-IMINES AND THEIR TAUTOMERS
    LANG, M
    LACROIX, A
    PONT, C
    FLEURY, JP
    HELVETICA CHIMICA ACTA, 1986, 69 (05) : 1025 - 1033
  • [4] SYNTHESIS OF 4(1H)-PYRIDONES BY CARBONYLATION OF 2-AZA-1,3-DIENES
    BARLUENGA, J
    CARLON, RP
    GONZALEZ, FJ
    FUSTERO, S
    TETRAHEDRON LETTERS, 1990, 31 (26) : 3793 - 3796
  • [5] AN EASY SYNTHESIS OF ELECTRON-WITHDRAWING SUBSTITUTED 2-AZA-1,3-DIENES AND THEIR 1,4-CYCLOADDITION WITH ENAMINES
    BARLUENGA, J
    TOMAS, M
    BALLESTEROS, A
    GOTOR, V
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (15) : 1195 - 1196
  • [6] 2-AZA-1,3-DIENES - A NEW AND SIMPLE METHOD FOR THE SYNTHESIS OF FUNCTIONALIZED PYRIDINE-DERIVATIVES
    BARLUENGA, J
    GONZALEZ, FJ
    CARLON, RP
    FUSTERO, S
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24): : 6751 - 6754
  • [7] TANDEM CYCLOADDITION REARRANGEMENT OF 2-AZA-1,3-DIENES - A SIMPLE AND EFFICIENT SYNTHESIS OF 1H-1,4-DIAZEPINE-7(6H)-THIONES
    BARLUENGA, J
    CARLON, RP
    GONZALEZ, FJ
    ORTIZ, FL
    FUSTERO, S
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (23) : 1704 - 1705
  • [8] Synthesis and reactivity of imines derived from bisphosphonates and 3-phosphorylated 2-aza-1,3-dienes
    Palacios, F
    Gil, MJ
    de Marigorta, EM
    Rodríguez, M
    TETRAHEDRON, 2000, 56 (34) : 6319 - 6330
  • [9] Synthesis of 3-phosphorylated 2-aza-1,3-dienes from imines derived from bisphosphonates.
    Palacios, F
    Gil, MJ
    de Marigorta, EM
    Rodríguez, M
    TETRAHEDRON LETTERS, 1999, 40 (12) : 2411 - 2414
  • [10] AN EFFICIENT AND GENERAL STRATEGY FOR THE SYNTHESIS OF 1,4-DIHYDRO-LAMBDA-3-AZAPHOSPHININES AND 1,4-DIHYDRO-LAMBDA-5-AZAPHOSPHININES FROM 2-AZA-1,3-DIENES
    BARLUENGA, J
    PALACIOS, F
    GONZALEZ, FJ
    FUSTERO, S
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (24) : 1596 - 1597
12345