A trend in the Chemistry of Ketengem-Dithiol Reaction and transformations

Acid catalyzed reaction of 1-(1H-indol-3-yl)-3,3-dimercaptoprop-2-en-1-one (1) with anthranilic acid (2) was achieved to produce 2-(1H-indol-3-yl)-4-oxo-1,4-dihydroquinoline-3-carbodithioic acid (3). Reactions of (1) with some amines e.g. p-chloroaniline (4) and o-aminophenol (5) in equimolar ratios and different reaction conditions were explored to produce (E)-3-((4-chlorophenyl)imino)-3-(1H-indol-3-yl)prop-1-ene-1,1-dithiol (6) and (E)-2-(benzo[d]oxazol-2(3H)-ylidene)-1-(1H-indol-3-yl)ethan-1-one  (7) respectively. While reaction of (1) with 3,5- dibromosalicyldehyde (8) or glucose (9), (6,8-dibromo-4-hydroxy-2-mercaptochroman-3-yl)(1H-indol-3-yl)methanone  (10) and 2-(dimercaptomethylene)-3,4,5,6,7,8-hexahydroxy-1-(1H-indol-3-yl)octan-1-one  (11) were obtained respectively. Also 5-(1H-indol-3-yl)-3H-1,2-dithiole-3-thione (12) was obtained from the reaction of (1) with P2S5. On treatment (12) with different reagents as 3,5-dibromosalicyldehyde (8) and anthranilic acid (2) gave the adducts  6,8-dibromo-3-(1H-indol-3-yl)-9a-mercapto-3H,9aH-[1,2]dithiolo[3,4-b]chromen-4-ol (13) and 3-(1H-indol-3-yl)-9a-mercapto-9,9a-dihydro-4H-[1,2]dithiolo[3,4-b]quinolin-4-one (14) respectively.  

Author(s): Salem E. Zayed, Awatef M. El Maghraby, Entesar A. Hassan and Hadir M. Mostafa

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