Synthetic approaches to 3-amino-1,4-naphthoquinone-2-carboxylic acid derivatives and photochemical synthesis of novel 1,4,5,10-tetrahydro-5,10-dioxo-2H-naphth[2,3-d][1,3]oxazine derivatives.
Synthesis of 3-alkylamino-1,4-naphthoquinone-2-carboxylic acid (2) was attempted. Although 3-(1-piperidinyl)-1,4-naphthoquinone-2-carboxylic acid (2a) was not obtained, probably because of its instability, the esters (18a, b) of 2a could be prepared. 2-Alkylamino-3-hydroxymethyl-1,4-naphthoquinones (9a-g) were photochemically cyclized to the 1,4,5,10-tetrahydro-5,10-2H-naphth[2,3-d][1,3]oxazines (19a-g), containing a novel heterocyclic ring system in moderate yields. Anti-bacterial activity of the prepared compounds was weak or insignificant.
Ohta
S
S
Kyoto Pharmaceutical University, Japan.
Hinata
Y
Y
Yamashita
M
M
Kawasaki
I
I
Shoji
T
T
Yoshikawa
H
H
Obana
Y
Y
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D010078:Oxazines / Q000138:chemical synthesis* / Q000494:pharmacology; D010777:Photochemistry
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D009285:Naphthoquinones; D010078:Oxazines