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Synthesis of novel pyrido[3′,2′:5,6]thiopyrano[3,2-b]indol-5(6H)-ones and 6H-pyrido[3′,2′:5,6]thiopyrano[4,3-b]quinolines, two new heterocyclic ring systems

✍ Scribed by Antonio Da Settimo; Anna María Marini; Giampaolo Primofiore; Federico Da Settimo; Silvia Salerno; Francesca Simorini; Gianluca Pardi; Concettina La Motta; Daniele Bertini

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
53 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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.

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