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The synthesis of novel polycyclic heterocyclic ring systems via photocyclization. 19. Thieno[3′,2′:4,5]thieno[2,3-c]-naphtho[1,2-f]quinoline, thieno[3′,2′:4,5]thieno[2,3-c]naphtho-[1,2-f][1,2,4]triazolo[4,3-a]quinoline and thieno[3′,2′:4,5]-thieno[2,3-c]naphtho[1,2-f]tetrazolo[1,5-a]quinoline

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


Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
351 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

Photocyclization of 3‐chloro‐N‐(3‐phenanthryl)thieno[2,3‐b]thiophene‐2‐carboxamide (5) yielded only one of the two possible structural isomers, thieno[3′,2′:4,5]thieno[2,3‐c]naphtho[1,2‐f]quinolin‐6(5__H__)‐one (6), which was further elaborated to afford the unsubstituted ring system 10, its triazole 11 and tetrazole 12. The structural confirmation of 10 was achieved by the total assignment of its ^1^H and ^13^C nmr spectra by the concerted utilization of two‐dimensional nmr spectroscopic methods.


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