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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 48, Number 6
JKCSEZ 48(6)
December 20, 2004 

 
Title
An Efficient Synthesis of Alkoxyallylthiopyridazine Derivatives from Maleic Anhydrides

Maleic Anhydrides로부터 Alkoxyallylthiopyridazines 유도체의 효과적 합성
Author
Jae In Lee, Young Sook Yun

이재인, 윤영숙
Keywords
알콕시알릴싸이오피리다진, 말레산 무수물, 치환 , Alkoxyallylthiopyridazines, Maleic Anhydrides, Substitution
Abstract
간염치료에 탁월한 효과를 나타내는 alkoxyallylthiopyridazine 유도체들이 maleic anhydrides로부터 합성되었다. 수용성 HCl에서 maleic anhydrides를 hydrazine monohydrate로 환류하면 dihydroxypyridazines이 얻어지며, 이 화합물을 phosphorus oxychloride로 반응시키면 dichloropyridazines으로 전환되었다. Dichloropyridazines에서 첫 번째 염소원자의 치환은 THF 용매에서 알코올성 sodium alkoxides에 의하여 선택적으로 일어나 alkoxy- chloropyridazines을 생성하며, 이 화합물은 lithium 2-propene-1-thiolate에 의하여 높은 수득율로 alkoxyallyl- thiopyridazines으로 전환되었다.

Alkoxyallylthiopyridazine derivatives which exhibit superior effect for the treatment of hepatic diseases were synthesized from maleic anhydrides. The reaction of maleic anhydrides with hydrazine monohydrate in aq HCl at reflux afforded dihydroxypyridazines, which were transformed to dichloropyridazines with phosphorus oxychloride. The substitution of the first chlorine atom in dichloropyridazines proceeded selectively with alcoholic sodium alkoxides in THF to afford alkoxychloropyridazines, which were converted to alkoxyallylthiopyridazines with lithium 2-propene-1-thiolate in high yields.

Page
609 - 615
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