Synthesis of [1,4]dioxino[2,3-c]quinolines and [1,4]dioxepino-[2,3-c]quinolines and their 1-sulfur analogues
✍ Scribed by Romana Hiessböck; Martin Kratzel
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1999
- Tongue
- English
- Weight
- 495 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
The synthesis of [1,4]dioxino[2,3‐c]quinolines and [1,4]dioxepino[2,3‐c]quinolines with restrained conformation of the piperidine ring, which represent 1,2,3,4‐tetrahydroquinolines containing two heteroatom substituents at positions 3 and 4, is described. In addition, the application of this approach for the synthesis of 1‐sulfur analogues is discussed. Both series are helpful tools for three‐dimensional quantitative structure‐activity relationship studies in the field of modulators of multidrug resistance.
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## Abstract Photocyclization of 3‐chloro‐__N__‐(3‐phenanthryl)naphtho[1,2‐__b__]thiophene‐2‐carboxamide (**12**) furnished only one of the two possible isomers, __i.e.__, naphtho[2′,1′:4,5]thieno[2,3‐__c__]naphtho[1,2‐__f__]quinolin‐6(5__H__)‐one (**13**), which was further elaborated to yield the
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