Optimisation of the synthesis of guanidines from amines via nitroguanidines using 3,5-dimethyl-N-nitro-1H-pyrazole-1-carboxamidine

被引：32

作者：

Castillo-Meléndez, JA ^{[1
]}

Golding, BT ^{[1
]}

机构：

[1] Univ Newcastle Upon Tyne, Sch Nat Sci Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

SYNTHESIS-STUTTGART | 2004年 / 10期

关键词：

guanidinylation; 3,5-dimethyl-N-nitro-1-pyrazole-1-carboxamidine; hydrogenolysis; ion exchange chromatography;

D O I：

10.1055/s-2004-829130

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the useful reagent for the preparation of guanidines, 3,5-dimethyl-N-nitro-1-pyrazole-1-carboxamidine (DMNPC), has been optimised. A detailed protocol for using this reagent for the preparation in pure form of a range of guanidines via nitroguanidines is described. A comparison has been made regarding efficiency between DMNPC and the guanidinylating reagents N,N'-bis-Boc-1-pyrazole-1-carboxamidine (2) and N,N'-bis-Boc-AP-triflylguanidine (3).

引用

页码：1655 / 1663

页数：9

共 36 条

[1]

ANDREWS E, 1949, J CHEM SOC, P2490

[2] Guanidine-substituted imidazoles as inhibitors of nitric oxide synthase [J].

Atkinson, RN ;

King, SB .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (20) :2953-2958

[3]

BAKER BR, 1964, J ORG CHEM, V29, P1047, DOI 10.1021/jo01028a015

[4] 1H-PYRAZOLE-1-CARBOXAMIDINE HYDROCHLORIDE - AN ATTRACTIVE REAGENT FOR GUANYLATION OF AMINES AND ITS APPLICATION TO PEPTIDE-SYNTHESIS [J].

BERNATOWICZ, MS ;

WU, YL ;

MATSUEDA, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2497-2502

[5] URETHANE PROTECTED DERIVATIVES OF 1-GUANYLPYRAZOLE FOR THE MILD AND EFFICIENT PREPARATION OF GUANIDINES [J].

BERNATOWICZ, MS ;

WU, YL ;

MATSUEDA, GR .

TETRAHEDRON LETTERS, 1993, 34 (21) :3389-3392

[6]

BOUKOUVALAS J, 1983, ANGEW CHEM S, V22, P860

[7] SAUREAMID-REAKTIONEN .27. UMSETZUNGEN MIT SAUREAMID-PHOSPHOROXYCHLORID-ADDUKTEN UND AMIDCHLORIDEN [J].

BREDERECK, H ;

BREDERECK, K .

CHEMISCHE BERICHTE-RECUEIL, 1961, 94 (08) :2278-2295

[8] A novel solid-phase synthesis of highly diverse guanidines:: Reactions of primary amines attached to the T2*linker [J].

Dahmen, S ;

Bräse, S .

ORGANIC LETTERS, 2000, 2 (23) :3563-3565

[9]

Davis TL, 1927, ORG SYNTH, V7, P46

[10] A new reagent and its polymer-supported variant for the amidination of amines [J].

Dräger, G ;

Solodenko, W ;

Messinger, J ;

Schön, U ;

Kirschning, A .

TETRAHEDRON LETTERS, 2002, 43 (08) :1401-1403

← 1 2 3 4 →