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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 53, Number 3
JKCSEZ 53(3)
June 20, 2009 

 
Title
Pyran and Pyridine as Building Blocks in Heterocyclic Synthesis

이중고리 합성에 블록제로서 이용된 피란과 피리딘
Author
Maher A El Hashash*, Abdallah A El Sawy, Abdelmonem M F Eissa, Mohammed S Sallam

Maher A El Hashash*, Abdallah A El Sawy, Abdelmonem M F Eissa, Mohammed S Sallam
Keywords
β-Aroylacrylic acid, 마이클 반응, 2-아미노피란, 2-아미노피리딘, 피리미딘, 말레암산 , β-Aroylacrylic acid, Michael reaction, 2-aminopyran, 2-aminopyridine, Pyrimidine, Maleamic-acid.
Abstract
현재 수행하는 작업은 피페리딘 또는 암모늄 아세테이트 존재하에서 malononitrile와 β- aroylacrylic acid 유도체의 DMF 용매조건에서 상호작용에 대한 연구이며, 형성된 화합물을 이용한 퓨즈 되고 단리된 이중고리화 시스템의 합성에 관한 것이다. β-aroylacrylic acid (3)이 DMF 용매와 피페리딘 촉매조건에malononitrile와 반응하여 4H-피란유도체(4)를 형성한다. 촉매를 암모늄 아세테이트로 바꿈 으로서 피리딘 유도체를 얻었다. 또한 N-말레암산 유도체 (19)와 (27)은 말레 무수물과 함께 (4)와 (5)의 반응을 경유하여 합성되었다. 마이클 첨가 반응에서 이용되는 메틸렌화합물에 관한 이 연구는 B-aroylacrylic acid의 경우와 유사하게 형성된 말레암산 유도체의 반응성에 대한 것이다.

The present work is devoted to study the interaction of β-aroylacrylic acid derivative (3) with malononitrile in (DMF) in the presence of piperidine and/or ammonium acetate, then using the formed compounds as starting materials for synthesizing fused and isolated heterocyclic systems. It has been established that the β-aroylacrylic acid (3) reacts with malononitrile in (DMF) in the presence of piperidine as a catalyst with the formation of 4H-pyran derivative (4). By changing the catalyst into ammonium acetate, pyridine derivative (5) has been obtained. Also the N-maleamic acid derivatives (19) and (27) have been synthesized via the interaction of (4) and (5) with maleic anhydride. The purpose of this step is to study the behavior of the formed maleamic acid derivatives ? as analogies of β-aroylacrylic acids ? towards different active methylene compounds under Michael addition reaction.

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308 - 324
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