Synthesis, structure, and some chemical properties of diferrocenyl-1,2,3-triazines

✍ Scribed by Elena I. Klimova; Tatiana Klimova; Marcos Flores Álamo; Daniel Méndez Iturbide; Marcos Martínez García

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2009
• Tongue: English
• Weight: 123 KB
• Volume: 46
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.93

✦ Synopsis

Abstract

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The reactions of 1‐amino‐2,3‐diferrocenylcyclopropenylium tetrafluoroborate (5a, 5b, 5c) or 2,3‐diferrocenyl‐1‐methylthiocyclopropenylium iodide with sodium azide afford 5‐amino‐4,6‐diferrocenyl‐1,2,3‐triazines (7a, 7b, 7c) or 5‐methylthio‐4,6‐diferrocenyl‐ and 4‐methylthio‐5,6‐diferrocenyl‐1,2,3‐triazines (8a and 8b), respectively. Their structures were established using spectroscopic methods and that of compound 8a was confirmed using X‐ray diffraction analysis. Triazines 5a, 5b, 5c react with alkyl iodides to yield N(2)‐ and N‐alkyl‐C(5)‐derivatives. Their alkaline hydrolysis results in 2‐methyl‐4,6‐diferrocenyl‐2,5‐dihydro‐1,2,3‐triazin‐5‐one (16) and 4,6‐diferrocenyl‐5‐hydroxy‐1,2,3‐triazine (17). J. Heterocyclic Chem., 46, 477 (2009).