Allylation of aldiminomercaptotriazinones using allyl halides and allylmetal compounds

✍ Scribed by Ashraf A. El-Shehawy

• Book ID: 102231754
• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 129 KB
• Volume: 14
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.10144

✦ Synopsis

Abstract

Allylation of 4‐amino‐3‐mercapto‐6‐methyl‐4__H__‐1,2,4‐triazin‐5‐one (1) and its arylideneamino derivatives 5 was performed through two different methods. Reaction of 1 and 5 with allylic bromides 2 in the presence of sodium ethoxide afforded a mixture of S‐ and N‐allylated products. Treatment of arylimines 5 with allylic zinc bromides 9 and triallylborane reagents 12 did not affect the hetero‐ring opening but the CN bond of the lateral chain underwent the addition reaction yielding the C‐allylated products 10. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:280–287, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10144