Studies using (E)-6-oxo-1-aryl-4-(2-N-piperidinyl)vinyl-1,6-dihydropyridazine-5-carbonitrile

被引：18

作者：

Abdelhamid, Ismail Abdelshafy ^{[1
]}

Ghozlan, Said Ahmed Soliman ^{[1
]}

Kolshorn, Heinz ^{[2
]}

Meier, Herbert ^{[2
]}

Elnagdi, Mohamed Hilmy ^{[1
]}

机构：

[1] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt

[2] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55099 Mainz, Germany

来源：

HETEROCYCLES | 2007年 / 71卷 / 12期

关键词：

4-methyl-6-oxopyridazine-5-carbonitrile; piperidinyl or morpholylenamine; pyrido[3,4-d]pyridazin-4-one; pyrazolylpyridazine;

D O I：

10.1016/S0385-5414(07)81199-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensing 1-aryl-4-methyl-1,6-dihydropyridazine-5carbonitrile with triethyl orthoformate and piperidine afforded the trans-enamine 2. This could be converted into pyrido[3,4-d]pyridazine 3 upon treatment with primary aromatic amines. Reacting 2 with hydrazonoyl chlorides 5 afforded 7 rather than 6. Compound 2 gives also pyrido[3,4-d]pyridazine 10 upon treatment with acetic acid and ammonium acetate. Compound 2 afforded N-aminopyrido[3,4-dlpyridazine 11 upon treatment with hydrazine hydrate. Compound 11 reacted with triethyl orthoformate to give [1,2,4]triazolo[2',3':1,2]pyrido[4,3-d]pyridazin-10-one 12 and can be acetylated to 13. Compound 2 could be coupled with p-chlorobenzenediazonium chloride to give the pyridazino[4,5-d]pyridazine 17.

引用

页码：2627 / 2637

页数：11