Heterocyclic synthesis containing bridgehead nitrogen atom: Synthesis of 3-[(2H)-2-oxobenzo[b]pyran-3-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazine and thiazole derivatives

The reaction of 2H‐2‐oxobenzo[b]pyran‐3‐hydrazide (2) with carbon disulfide in basic DMF afforded potassium thiocarbamate 3, which readily underwent heterocyclization upon its reaction with hydrazine and/or phenacyl bromide to yield 1,2,4‐tiazole (4) and thiazole 7 derivatives, respectively. Condens...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Heteroatom chemistry 2003, Vol.14 (2), p.114-120
Hauptverfasser: Raslan, M. A., Khalil, M. A.
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The reaction of 2H‐2‐oxobenzo[b]pyran‐3‐hydrazide (2) with carbon disulfide in basic DMF afforded potassium thiocarbamate 3, which readily underwent heterocyclization upon its reaction with hydrazine and/or phenacyl bromide to yield 1,2,4‐tiazole (4) and thiazole 7 derivatives, respectively. Condensation of 4 with substituted phenacyl bromide and/or chloranil gave 1,2,4‐triazole[3,4‐b]thiadiazine (5a,b) and 3,10‐bis‐[2H‐2‐oxobenzo[b]pyran‐3‐yl]‐6,13‐dichloro‐bis‐1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazino[5′,6′‐b:5′,6′‐e]cyclohexa‐1,4‐diene (6), respectively. Cyclization of thiosemicarbazide 10 by refluxing it in sodium hydroxide and/or phosphoryl chloride afforded triazole 13 and thiadiazole 15 derivatives, respectively. Also, 10 reacted with phenacyl bromide in the presence of anhydrous sodium acetate to give the oxothiazolidine derivative 17. The structure of the synthesized compounds were confirmed by elemental analyses, IR, 1H NMR, and mass spectra. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:114–120, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10109
ISSN:1042-7163
1098-1071
DOI:10.1002/hc.10109