Syntheses of a Novel Class of 5/6/5-Heterocycles: Convenient Routes from Aldehydes to Bis(1,3,4-thiadiazolo)-1,3,5-triazinium Halides

✍ Scribed by Ernst Anders; Kurt Wermann; Bernd Wiedel; Wolfgang Günther; Helmar Görls

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 174 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199812)1998:12<2923::aid-ejoc2923>3.0.co;2-2

✦ Synopsis

Novel 5/6/5 heterocycles, 1,3,4-thiadiazolo[3,2-a]-1,3,4-latter show that both sp 2 -C atoms C(10) and C(12) of 7 are significantly positively charged and, therefore, exhibit thiadiazolo[3,2-d]-1,3,5-triazinium halides 7, have been synthesized by the reaction of 2-amino-1,3,4-thiadiazoles 6 electrophilic properties towards the primary amino group of the amino-thiadiazoles 6. In the course of a multi-step with either 1-(haloalkyl)pyridinium halides 4 or N,NЈmethylenebis(pyridinium) dibromides 5. The tricyclic reaction cascade of the 6/7 mixture, novel multi-aza/thia heterocycles 8 are formed. The structures of the latter compounds 7 are generated in the course of several successive reaction steps in which specific proton migrations, compounds have been confirmed by X-ray analysis as well as by detailed experimental and theoretical NMR-bond-breaking and bond-forming processes occur. The structures 7 have been verified by spectral data ( 1 H and 13 C spectroscopic studies. NMR, MS), X-ray analysis and ab initio calculations. The