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Synthesis of New Crown Ethers Containing Benzothiazole Group

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Àå½ÂÇö ( Chang Seung-Hyun ) - Taegu University Department of Chemistry
¿¬¾Ö¼÷ ( Yeon Ae-Sook ) - Taegu University Department of Chemistry
Á¤±¤º¸ ( Chung Kwang-Bo ) - Hanseo University Department of Chemical Engineering

Abstract

Crown °í¸® ±Ù¹æ¿¡ Áú¼Ò, Ȳ¿øÀÚ ¸¦ Æ÷ÇÔÇÏ´Â »õ·Î¿î2Á¾ÀÇ crown ether¸¦ ÇÕ¼ºÇÏ¿´´Ù. 4'-Benzothiazolylbenzo-12-crown-4 (1) 4'-Benzothiazolylbenzo-15-crown-5 (2)´Â °¢°¢ 4'-formylbenzo-12-crown-4 (3)¹×4'-formylbenzo-15-crown-5 (4)¿Í 2-aminothiophenol°úÀÇ ¹ÝÀÀ¿¡ ÀÇÇØ ÇÕ¼ºÇÏ¿´´Ù. (3)°ú(4)´Â 3, 4-dihydroxybenzaidehyde¿Í tri-¹× tetraethyleneglycolditosylate¿ÍÀÇ ¹ÝÀÀ¿¡ ÀÇÇØ ÇÕ¼ºÇÏ¿´´Ù. Triethyleneglycolditosylate¿Í tetraethyleneglycol ditosylate´Â NaOH Á¸ÀçÇÏ¿¡¼­ triethyleneglycol, tetraethyyleneglyco.°ú p-toluenesulfonyl chlorideÀÇ ¹ÝÀÀ¿¡ ÀÇÇØ ÇÕ¼ºÇÏ¿´´Ù.

Two new crown ethers containing nitrogen and sulfur atoms adjacent to the crown rings were prepared. 4'-Benzothiazolylbenzo-12-crown-4 (1) or 4'-benzothiazolylbenzo-15-crown-5 (2) were synthesized by reaction of 2-aminothiophenol with 4'-formylbenzo-12-crown-4 (3) or 4'-formylbenzo-15-crown-5 (4) respectively. (3) and (4) were obtained by reaction of 3, 4-dihydroxybenzaldehyde with tri- or tetraethyleneglycol ditosylate. Triethyleneglycol ditosylate or tetraethyleneglycol ditosylate were synthesized by reaction of p-toluenesulfonylchloride with triethyleneglycol or tetraethyleneglycol in the presence of sodium hydroxide.

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