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1,4,5,8-Tetraazafulvalenes – A Convenient One-Pot Synthesis and Their Conversion to Fused Ring Systems

✍ Scribed by Käpplinger, Christian ;Beckert, Rainer ;Günther, Wolfgang ;Görls, Helmar

Book ID
102901234
Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
664 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Cycloacylation of formamidine with bisimidoyl chlorides of oxalic acid yields the new 1,4,5,8‐tetraazafulvalenes 4 via dimerization of carbenoid intermediates. The high symmetry of the stable heterofulvalenes as well as their dye character is confirmed by NMR and UV/Vis spectral data. Whereas methylation of these substrates leads to a mixture of diastereomeric tetramethyl derivatives 9a, b, cyclization with thiophosgene or triethyl orthoformate gives mainly the fused‐ring derivatives of 2__H__‐imidazole 10 and 12a, b, respectively. In the case of 12a, the X‐ray crystal structure reveals the approximately ideal planarity of the central tetraazafulvalene subunit.

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