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Synthesis of novel pyrido[3′,2′:5,6]thiopyrano[3,2‐ b ]indol‐5(6 H )‐ones and 6 H ‐pyrido[3′,2′:5,6]thiopyrano[4,3‐ b ]quinolines, two new heterocyclic ring systems
Author(s) -
Da Settimo Antonio,
Marini Anna María,
Primofiore Giampaolo,
Da Settimo Federico,
Salerno Silvia,
Simorini Francesca,
Pardi Gianluca,
La Motta Concettina,
Bertini Daniele
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390522
Subject(s) - chemistry , indole test , stereochemistry , medicinal chemistry
The synthesis of new pyrido[3′,2′:5,6]thiopyrano[3,2‐ b ]indol‐5(6 H )‐ones was accomplished by the Fischer‐indole cyclization of some 2,3‐dihydro‐3‐phenylhydrazonothiopyrano[2,3‐ b ]pyridin‐4(4 H )‐ones, obtained from the 2,3‐dihydro‐3‐hydroxymethylenethiopyrano[2,3‐ b ]pyridin‐4(4 H )‐one, by the Japp‐Klingemann reaction. 6 H ‐Pyrido[3′,2′:5,6]thiopyrano[4,3‐ b ]quinolines were obtained by reaction of 2,3‐dihydrothiopyrano‐[2,3‐ b ]pyridin‐4(4 H )‐ones with o ‐aminobenzaldehyde or 5‐substituted isatins. The preparation of some derivatives, functionalized with an alkylamino‐substituted side chain, is also described.