Solvent-free Route to β-Enamino Dichloromethyl Ketones and Application in the Synthesis of Novel 5-Dichloromethyl-1H-pyrazoles

被引：8

作者：

Martins, Marcos A. P. ^{[1
]}

Peres, Rodrigo L. ^{[1
]}

Frizzo, Clarissa P. ^{[1
]}

Scapin, Elisandra ^{[2
]}

Moreira, Dayse N. ^{[1
]}

Fiss, Gabriela F. ^{[1
]}

Zanatta, Nilo ^{[1
]}

Bonacorso, Helio G. ^{[1
]}

机构：

[1] Univ Fed Santa Maria, Dept Quim, Nucleo Quim Heterociclos, BR-97105900 Santa Maria, RS, Brazil

[2] Univ Fed Tocantins, Lab Quim, Plamas, TO, Brazil

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2009年 / 46卷 / 06期

关键词：

HALOACETYLATED ENOL ETHERS; RING-CLOSURE REACTIONS; REGIOSPECIFIC SYNTHESIS; TRIFLUOROMETHYL KETONES; METHYL-ESTERS; IONIC LIQUID; PYRAZOLES; CONDENSATION;

D O I：

10.1002/jhet.227

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient procedure to prepare a series of five 4-amino-1,1-dichloro-3-penten-2-ones [CHCl2C(O)CH=C(Me)(NRR2)-R-1, where R-1/R-2 = H/Ph, H/Bn, H/CH2CH2OH, -(CH2)(4)-, -(CH2)(2)O(CH2)(2)] from the solvent-free reaction of 1,1-dichloro-4-methoxy-3-penten-2-one with primary and secondary amines is reported. 1,1-Dichloro-4-methoxy-3-penten-2-one was reacted with hydrazine hydrochloride, phenylhydrazine hydrochloride and semicarbazide hydrochloride to obtain 5-dichloromethyl-3-methylpyrazoles. Aminoguanidine hydrochloride and 1,2-dimethylhydrazine dihydrochloride were also reacted with 1,1-dichloro-4-methoxy-3-penten-2-one to obtain 5-dichloromethyl-3-methylpyrazoline and 5-dichloromethyl-1,2,3-trimethyl pyrazolium chloride, respectively. All cyclocondensation reactions were performed in one-pot procedures.

引用

页码：1247 / 1251

页数：5

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