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The synthesis of novel polycyclic heterocyclic ring systems via photocyclization. 23 . Naphtho[2′,1′:4,5]thieno-[2,3-c]naphtho[2,1-f]quinoline

✍ Scribed by Jiann-Kuan Luo; Maria-Paz Cabal; Ronald F. Federspiel; Raymond N. Castle


Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
54 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

A previously unknown heterocyclic ring system, naphtho[2′,1′:4,5]thieno[2,3‐c]naphtho[2,1‐f]quinoline (14), was synthesized via oxidative photocyclization of 3‐chloro‐N‐(2‐phenanthryl)naphtho[1,2‐b]‐thiophene‐2‐carboxamide (9). Further elaboration of the lactam 10 yielded the unsubstituted ring system 14. Structural confirmation of compound 14 was accomplished by a total assignment of its ^1^H and ^13^C nmr spectra utilizing the concerted two‐dimensional nmr spectroscopic methods.


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## Abstract Photocyclization of 3‐chloro‐__N__‐(9‐phenanthryl)benzo[__b__]‐thiophene‐2‐carboxamide (**3**) and 3‐chloro‐__N__‐(9‐phenanthryl)‐naphtho[1,2‐__b__]thiophene‐2‐carboxamide (**10**) yielded dibenzo[__f,h__]benzothieno[2,3‐__c__]‐quinolin‐10(9__H__)‐one (**4**) and dibenzo[__f,h__]naphtho