THE MECHANISM OF THE THERMOLYTIC RING-OPENING OF 5-AZIDO-4-FORMYL-3-METHYL-1-PHENYLPYRAZOLE

被引：6

作者：

BECHER, J

BEGTRUP, M

GJERLOV, A

LARSEN, S

DEHAEN, W

CHRISTENSEN, LK

机构：

[1] ROYAL DANISH SCH PHARM, DEPT MED CHEM,UNIV PK 2, DK-2100 COPENHAGEN, DENMARK

[2] ODENSE UNIV, DEPT CHEM, DK-5230 ODENSE, DENMARK

[3] LAB ORGAN SYNTH, B-3001 HEVERLEE, BELGIUM

[4] UNIV COPENHAGEN, DEPT CHEM, DK-2100 COPENHAGEN, DENMARK

来源：

ACTA CHEMICA SCANDINAVICA | 1995年 / 49卷 / 01期

关键词：

D O I：

10.3891/acta.chem.scand.49-0057

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Thermolysis of 5-azido-4-formyl-3-methyl-1-phenylpyrazole 4 produces the (4-cyanopyrazol-3-ylmethyl)pyrazoles 3 and 6. 2-Cyano-3-phenylazo-2-butenal 2 was detected by H-1 NMR spectroscopy during the reaction. The products 3 and 6 and other rearrangement products obtained when 5-chloro-4-formylpyrazoles are reacted with azide ion all seem to be formed by a common mechanism, via substituted 2-cyano-3-azo propenals or a zwitterionic intermediate. The nature of the products is determined by the position of nucleophilic attack at the intermediate. Structural characterization of the products has been obtained by NMR spectroscopy and single-crystal X-ray crystallography.

引用

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页码：57 / 63

页数：7

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