| Summary: | 碩士 === 中原大學 === 化學研究所 === 96 === The reaction of 4-ethoxyl-1-ethoxycarbonylazulene and hydrazine to give 1-ethoxycarbonyl-4-hydrazoazulene derivatives, and then reacted with ketones to affored 1-ethoxycarbonyl-4-hydrazoazulene derivatives, while proceed with Fischer indole reaction to afford 7-ethoxycarbonyl- azuleno [4,5-b] pyrrole which is used phosphorus chloride oxide reagent.
1-ethoxycarbonyl-3-alkyl-4-hydrazoazulene was synthesized by 4-hydrazoazulene derivatives with phosphorus chloride oxide, which was further proceed with Fischer indole reaction. The ring-closed was 4-position and 5-position of azulene. The 3-substituted azulene was exist while the aldehydes substituted to 2-position of azulene, and the 3-position was no substituted while the aldehydes substituted to 3-position of azulene.
4-amino-1-ethoxycarbonylazulene was synthesized by substitution of 4-ethoxyl-1-ethoxycarbonylazulene with amino groups and reacted with acetylate reaction to give 4-amino-3-formyl-1-ethoxylcarbonylazulene. The condensation reaction shows that 4-amino-3-formyl-1-ethoxyl carbo- nylazulene reacted with ketones , which was further proceeded with the Michael addition to affored 4-ethoxycarbonyl-1-azacyclopent[8,1-cd]azulene.
4-amino-3-formyl-1-ethoxylcarbonylazulene reacted with ECA or DEM which proceed the condensation reaction, and the Michael addition to affored 1H-azuleno[8,1-bc]azepine.
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