Rapid synthesis of tetrahydro-4H-pyrazolo[1,5-a]diazepine-2-carboxylate

被引：23

作者：

Cvetovich, RJ ^{[1
]}

Pipik, B ^{[1
]}

Hartner, FW ^{[1
]}

Grabowski, EJJ ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Sharp & Dohme Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 31期

关键词：

aminohydrazines; hydroxyhydrazines; pyrazole formation; pyrazolo-diazepine;

D O I：

10.1016/S0040-4039(03)01417-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrazines condense with dimethyl 2-pyrrolidino-4-oxo-2-pentenedioate in the presence of aq. HCl to form N-substituted pyrazole-3,5-dicarboxylates 2. Complex bicyclic derivatives, such as pyrazolo-oxazine 3a, pyrazolo-oxazepine 3b, pyrazolopyrazine 4a, and pyrazolo-diazepine 4b, were generated using 2-hydrazinoethanol, 3-hydrazinopropanol, 2-hydrazinoethylamine, and 3-hydrazinopropylamine. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：5867 / 5870

页数：4

共 11 条

[1]

ARNOLD Z, 1990, SYNTHESIS-STUTTGART, P39

[2] Non-peptide glycoprotein IIb/IIIa inhibitors .17. Design and synthesis of orally active, long-acting non-peptide fibrinogen receptor antagonists [J].

Askew, BC ;

Bednar, RA ;

Bednar, B ;

Claremon, DA ;

Cook, JJ ;

McIntyre, CJ ;

Hunt, CA ;

Gould, RJ ;

Lynch, RJ ;

Lynch, JJ ;

Gaul, SL ;

Stranieri, MT ;

Sitko, GR ;

Holahan, MA ;

Glass, JD ;

Hamill, T ;

Gorham, LM ;

Prueksaritanont, T ;

Baldwin, JJ ;

Hartman, GD .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (12) :1779-1788

[3] SELECTIVE SEQUENTIAL DEMASKING OF THE ESTER FUNCTIONS OF 1-METHYL-3,4,5-TRIS(METHOXYCARBONYL)PYRAZOLE [J].

CHAMBERS, D ;

DENNY, WA ;

BUCKLETON, JS ;

CLARK, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24) :4736-4738

[4] TRANSFORMATIONS OF PYRROLIDINE ENAMINONES YIELDING (OMEGA-AMINOPROPYL)-PYRAZOLES [J].

DANNHARDT, G ;

GEYER, Y ;

MAYER, KK ;

OBERGRUSBERGER, R .

ARCHIV DER PHARMAZIE, 1988, 321 (01) :17-19

[5] HYDRAZINOALKANOLS [J].

GEVER, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (05) :1283-1285

[6] A highly convergent synthesis of a fibrinogen receptor antagonist [J].

Hartner, FW ;

Cvetovich, RJ ;

Tsay, FR ;

Amato, JS ;

Pipik, B ;

Grabowski, EJJ ;

Reider, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7751-7755

[7] SYNTHESIS AND CHARACTERIZATION OF MASKED AMINOPYRAZOLECARBOXYLIC ACID SYNTHONS [J].

LEE, HH ;

CAIN, BF ;

DENNY, WA ;

BUCKLETON, JS ;

CLARK, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (02) :428-431

[8] Synthesis of pyrazoles [J].

Makino, K ;

Kim, HS ;

Kurasawa, Y .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (03) :489-497

[9] Synthesis of pyrazoles and condensed pyrazoles [J].

Makino, K ;

Kim, HS ;

Kurasawa, Y .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (02) :321-332

[10] HETEROANNULATED-9,10-ANTHRACENEDIONES - THE SYNTHESIS OF SUBSTITUTED 5-CHLOROANTHRA[1,9-CD]PYRAZOL-6(2H)-ONES AND 7-CHLOROANTHRA[1,9-CD]PYRAZOL-6(2H)-ONES, PRECURSORS TO ANTICANCER ANTHRAPYRAZOLES [J].

SHOWALTER, HDH ;

JOHNSON, JL ;

HOFTIEZER, JM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (05) :1491-1501

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