Synthesis and physiological activity of thiophenes and furans with 3- and 4-methoxyacetophenone derivatives.
The synthesis and physiological activity of thiophenes and furans with methoxyacetophenone derivatives were examined. 3-Methoxyacetophenone (1) and 4-methoxyacetophenone (2) were converted, respectively, to the oximes (3) and (4) by oximation with hydroxylamine hydrochloride, and to the primary amines (5) and (6) by reduction with LiAlH(4). The primary amine derivatives were further converted into the thiophene and furan compounds (5a) approximately (5h) and (6a) approximately (6h), respectively. Bioassay of these compounds (5a) approximately (5h) and (6a) approximately (6h) on the germination of lettuce(Lactuca satiba) seeds showed that compound (5b) exhibits growthpromoting activity.
Tachibana
Shinya
S
Konan Chemical Industry Co., Ltd., Nakagawa, Takatsuki, Osaka 569-0066, Japan. shinyatachibana@u01.gate01.com
Gotou
Takashi
T
Nomura
Masato
M
D000098:Acetophenones / Q000737:chemistry; D017607:Aluminum Compounds / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis; D000840:Anisoles / Q000737:chemistry; D001681:Biological Assay; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018525:Germination / Q000187:drug effects*; D006540:Herbicides / Q000138:chemical synthesis* / Q000494:pharmacology*; D019811:Hydroxylamine / Q000737:chemistry; D018545:Lactuca / Q000187:drug effects; D018020:Lithium Compounds / Q000737:chemistry; D010091:Oximes / Q000138:chemical synthesis; D012639:Seeds / Q000187:drug effects; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000098:Acetophenones; D017607:Aluminum Compounds; D000588:Amines; D000840:Anisoles; D005663:Furans; D006540:Herbicides; D018020:Lithium Compounds; D010091:Oximes; D013876:Thiophenes; C046029:4-acetylanisole; D019811:Hydroxylamine; C042073:lithium aluminum hydride