New practical synthesis of indazoles via condensation of o-fluorobenzaldehydes and their o-methyloximes with hydrazine

被引：95

作者：

Lukin, Kirill ^{[1
]}

Hsu, Margaret C. ^{[1
]}

Fernando, Dilinie ^{[1
]}

Leanna, M. Robert ^{[1
]}

机构：

[1] Abbott Labs, GPRD Proc Res & Dev, N Chicago, IL 60064 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 21期

关键词：

EFFICIENT SYNTHESIS; INHIBITORS; HETEROCYCLES; POTENT; DERIVATIVES; SYNTHASE;

D O I：

10.1021/jo0613784

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of o-fluorobenzaldehydes and their O-methyloximes with hydrazine has been developed as a new practical synthesis of indazoles. Utilization of the methyloxime derivatives of benzaldehydes (in the form of the major E-isomers) in this condensation effectively eliminated a competitive Wolf-Kishner reduction to fluorotoluenes, which was observed in the direct preparations of indazoles from aldehydes. Reaction of Z-isomers of methyloximes with hydrazine resulted in the formation of 3-aminoindazoles via a benzonitrile intermediate.

引用

页码：8166 / 8172

页数：7

共 37 条

[1] PHASE-TRANSFER CATALYZED SYNTHESIS OF INDAZOLES FROM ORTHO-ALKYLBENZENEDIAZONIUM TETRAFLUOROBORATES
BARTSCH, RA
YANG, IW
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (04) : 1063 - 1064
[2] PHASE-TRANSFER-CATALYZED GOMBERG-BACHMANN SYNTHESIS OF UNSYMMETRICAL BIARENES - A SURVEY OF CATALYSTS AND SUBSTRATES
BEADLE, JR
KORZENIOWSKI, SH
ROSENBERG, DE
GARCIASLANGA, BJ
GOKEL, GW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) : 1594 - 1603
[3] Behr L. C., 1969, PYRAZOLES PYRAZOLINE, P28
[4] KINETICS, STOICHIOMETRY AND MECHANISM IN BROMINATION OF AROMATIC HETEROCYCLES .3. AQUEOUS BROMINATION OF INDAZOLE
BOULTON, BE
COLLER, BAW
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (11) : 2343 - 2347
[5] The recent impact of solid-phase synthesis on medicinally relevant benzoannelated nitrogen heterocycles
Bräse, S
Gil, C
Knepper, K
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) : 2415 - 2437
[6] Caron S, 1999, SYNTHESIS-STUTTGART, P588
[7] Non-covalent thrombin inhibitors featuring P3-heterocycles with P1-bicyclic arginine surrogates
Cui, JRJ
Araldi, GL
Reiner, JE
Reddy, KM
Kemp, SJ
Ho, JZ
Siev, DV
Mamedova, L
Gibson, TS
Gaudette, JA
Minami, NK
Anderson, SM
Bradbury, AE
Nolan, TG
Semple, JE
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (20) : 2925 - 2930
[8] Synthesis and structure-activity studies of novel orally active non-terpenoic 2,3-oxidosqualene cyclase inhibitors
Dehmlow, H
Aebi, JD
Jolidon, S
Ji, YH
von der Mark, EM
Himber, J
Morand, OH
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (15) : 3354 - 3370
[9] NEW HETEROAROMATIC COMPOUNDS .17. FLUORO DERIVATIVES OF 10-METHYL-10,9-BORAZAROPHENANTHRENE
DEWAR, MJS
GRISDALE, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (07) : 1759 - &
[10] Elguero J., 1984, COMPREHENSIVE HETERO, V5, P167, DOI DOI 10.1016/B978-008096519-2.00072-2

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