Synthese und Reaktionsverhalten neuer tri- sowie tetracyclischer Schwefelanaloga des Indols, 2. Mitt

Synthesis and Reactivity of New Tri- and Tetracyclic Sulfur Analogues of Indole, II: The ketone oxime 1 was rearranged to the lactam 2 . Hydrolysis lead to the amino acid 3b and to the salt 3a . With “Meerwein salt” we received the lactimether 4 , with P₄S₁₀ the thiolactam 5 , with methyl iodide the thiolactim ether 6 . Compound 4 reacted with malodinitril to yield the derivative 7 . From 4 and 1-phenyl-3-methyl-5-pyrazolone we received compound 8 . Substituted hydrazides react with 4 to yield compounds 9a–9h . After heating of 9e, 9d, 9f and 9g we isolated 10, 11, 12 and 13 , respectively. Compound 2 reacts with PCI₅ and NaN₃ to yield the tetrazole 14 . Acylation of benzothiophene (15) with the ester chloride 16 leads to a mixture of the esters 17 and 18 from which we received the acids 19 and 20 . Cyclisation leads to the ketones 21 and 22 . The tropone derivative 28 was synthesized from thiophenol 23 via compound 25 , acid 26 and ketone 27 .