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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 47, Number 6
JKCSEZ 47(6)
December 20, 2003 

 
Title
Microwave Assisted Reaction of Condensed Thiophenes With Electron Poor Olefins

Microwave Assisted Reaction of Condensed Thiophenes With Electron Poor Olefins
Author
Khadijah M. Al-zaydi*, Mohamed H. Elnagdi

Khadijah M. Al-zaydi*, Mohamed H. Elnagdi
Keywords
마이크로웨이브, 싸이오펜, 고리첨가반응 , Microwave, Thiophene, Cycloaddition Reaction
Abstract
아미노싸이에노피리다진(1a, b)과 아미노싸이에노쿠마린(2)은 DMFDMA와 축합반응을 하여 아미딘(3a, b)을 형성한다. 이 화합물들을 N-페닐말레이마이드와 반응시키면 화합물 9와 10이 얻어진다. 반면에 3a, b, 4, 18, 19, 20을 말레산 무수물과 반응시키면 포밀 유도체인 5a, b, 6, 21, 22, 23 들이 얻어진다. 아미딘 화합물 3a, b 를 다이에틸 퓨마레이트와 반응시키면 가수분해산물인 아미딘 14를 거쳐 11이 얻어진다. N-페닐말레이마이드를 마이크로웨이브 오븐에서 반응시키면 [2+2]와 [2+2+2] 고리첨가반응 산물이 얻어진다.

Aminothienopyridazines 1a, b and aminothienocoumarin 2 condensed with DMFDMA to yield amidines 3a, b and 4. These compounds reacted with N-phenylmaleimide to yield 9 and 10. On the other hand reacting 3a, b, 4, 18, 19 and 20 with maleic anhydride afforded only the formylated derivatives 5a, b, 6, 21, 22 and 23 respectively. The reaction of 3a, b with diethyl fumarate afforded 11, formed most likely via hydrolysis of the amidine 14 during working up the reaction mixture. Irradiation of N-phenylmaleimide in microwave oven afforded [2+2] and [2+2+2] cycloaddition product.

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