Synthesis of functionalised pyrazolones and imidazolines/imidazoles through divergent cyclisation reactions

被引：23

作者：

Abbiati, G

Arcadi, A

Attanasi, OA

De Crescentini, L

Rossi, E

机构：

[1] Univ Aquila, Fac Sci, Dipartimento Chim Ingn Chim & Mat, I-67100 Laquila, Italy

[2] Univ Milan, Fac Farm, Ist Chim Organ, I-20133 Milan, Italy

[3] Univ Urbino, Fac Sci, Ist Chim Organ, I-61029 Urbino, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 10期

关键词：

alpha-aminohydrazones; pyrazolones; copper complexes; imidazolines/imidazoles;

D O I：

10.1016/S0040-4020(01)00022-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The base-promoted reactions of easily accessible alpha -aminohydrazones represent a simple and efficient method for the preparation of both I-substituted and 1-unsubstituted-4-aminocarbonyl-1H-pyrazol-5(2H)-ones, whereas the copper promoted reactions provide a divergent facile regiocontrolled synthesis of the imidazoline/imidazole ring system. The copper-promoted reaction of the alpha -benzylaminohydrazone produces a 2-oxo-1,4-diazadiene derivative. Finally, the imidazolines can be easily hydrolyzed to alpha -ketohydrazones. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2031 / 2038

页数：8

共 55 条

[1] ACHESON RM, 1977, INTRO HETEROCYCLIC C, P362
[2] THE ASYMMETRIC KHARASCH REACTION - CATALYTIC ENANTIOSELECTIVE ALLYLIC ACYLOXYLATION OF OLEFINS WITH CHIRAL COPPER(I) COMPLEXES AND TERT-BUTYL PERBENZOATE
ANDRUS, MB
ARGADE, AB
CHEN, X
PAMMENT, MG
[J]. TETRAHEDRON LETTERS, 1995, 36 (17) : 2945 - 2948
[3] Base or copper promoted annulation reactions of alpha-aminohydrazones
Arcadi, A
Attanasi, OA
DeCrescentini, L
Rossi, E
[J]. TETRAHEDRON LETTERS, 1997, 38 (13) : 2329 - 2332
[4] Arcadi A, 1999, EUR J ORG CHEM, V1999, P3117
[5] Arcadi A, 1996, SYNTHESIS-STUTTGART, P533
[6] ATTANASI O, 1984, SYNTHESIS-STUTTGART, P422
[7] ATTANASI O, 1984, SYNTHESIS-STUTTGART, P671
[8] ATTANASI O, 1984, SYNTHESIS-STUTTGART, P873
[9] Attanasi O. A., 1986, ORG PREP PROCED INT, V18, P299
[10] 2-oxohydrazones, 4-hydrazono-1H-pyrazol-5-ones, and derived products by air oxidation of 1,2-hydrazino-hydrazones
Attanasi, OA
De Crescentini, L
Filippone, P
Foresti, E
Mantellini, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (09) : 2820 - 2823

← 1 2 3 4 5 6 →