생명과학회지 (Journal of Life Science)

  • 제13권6호
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  • Pages.836-842
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  • 2003
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  • 1225-9918(pISSN)
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  • 2287-3406(eISSN)
한국생명과학회 (Korean Society of Life Science)
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Dipyrrolylbenzene들의 합성에 관한 연구

A Study on the Synthesis of Dipyrrolylbenzenes

  • 발행 : 2003.12.01
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초록

1,2-phenylenediamino과 2,5-dimethoxytetrahydro- furan을 빙초산 용매하에서 1-(2-aminophenyl)- pyrrole 5를 합성하였다. 1,3-phenylenediamine과 2,5-dimethoxytetrahydrofuran을 빙초산을 사용하여 1-(3-aminophenyl)pyrrole 7과 1,3-dipyrrolyl-benzene 8을 합성하였다. 1,4-phenyl-enediamine과 2,5-dimethoxytetrahydrofuran을 빙초산을 사용하여 1,4-dipyrrolylbenzene 10을 합성하였다. 1,2-phenylenediamine, 1,3-phenylenediamine 그리고 1,4-phenyl-enediamine과 2,5-dimethoxytetra- hydrofuran을 (가) 빙초산 대신, (나) 용매없이, (다) acrylic acid, (라) silica gel, (마) acrylic acid와 silicagel, 그리고 (바) silica gel과 acetic acid를 사용하여 각각 반응시켜 그에 상응하는 amino-phenylpyrroles 5, 7과 dipyrrolylbenzenes 8, 10을 합성하였다. 여러 가지 방법 중 (마) silicagel과 acetic acid를 사용한 경우에 dipyrrolylbenzenes 8, 10의 합성에 관한 반응성이 가장 좋았다. 또한 dicarbazolylbenzene을 합성하기 위한 전단계로 9-phenylcarbazole 11을 합성하였다.

1-(2-Aminophenyl)pyrrole 5 was synthesized by using 1,2-phenylenediamine with 2,5-dimethoxy-tetrahydrofuran in glacial acetic acid. 1-(3-Aminophenyl)pyrrole 7 and 1,3-dipyrrolylbenzene 8 were obtained by using 1,3-phenylene-diamine with 2,5-dimethoxytetrahydrofuran in glacial acetic acid. 1,4-Dipyrrolylbenzene 10 was synthesized by using 1,4-phenylenediamine with 2,5-dimethoxy-tetrahydrofuran in glacial acetic acid. Aminophenylpyrroles 5, 7 and dipyrrolylbenzenes 8, 10 were respectively synthesized by treatment of 1,2-phenylenediamine, 1,3-phenylenediamine, 1,4-phenylene-diamine and 2,5-dimethoxytetrahydrofuran in (1) no solvent or (2) acrylic acid or (3) silica gel or (4) acrylic acid and silica gel or (5) silica gel and glacial acetic acid instead of glacial acetic acid. The best yield for dipyrrolylbenzene 10 was obtained when silica gel and glacial acetic acid was used. 9-Phenyl-carbazole 11 was synthesized by treatment of 1-phenylpyrrole with 2,5-dimethoxy-tetrahydrofuran in glacial acetic acid.

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