Synthesis of N-substituted amidinoheteroles and their reactivity towards Burgess reagent. (2nd January 2020)

• Record Type: Journal Article
• Authors: Uchiyama, Yosuke; Kimura, Shinobu; Kurotaki, Takanori; Sawamura, Yukihiro; Kikuchi, Yuichi; Abe, Shinya; Runyon, Jason W.; Dolphin, Joshua S.; Schinnen, Christoph; Arduengo III, Anthony J.
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 195:Number 1(2020)
• Page Start: 3
• Page End: 6
• Publication Date: 2020-01-02
• Subjects: Amidinoheterole -- amidinium heterolides -- urgess reagent -- X-ray crystallographic analysis -- heterocycles; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2019.1669602
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: N -Substituted amidinoimidazoles and amidinopyrroles were synthesized by the reaction of 2-cyanoimidazole and 2-cyanopyrrole with the corresponding ammonium salts in the presence of AlMe3 in toluene under reflux conditions. With the aim to investigate the transformation of the N -substituted amidino group to isonitrilium ion, N -mesitylamidinoimidazole and N -diisopropylphenylamidinopyrrole were allowed to react with the Burgess reagent. Instead of the desired deamination product, 1, 2, 4, 6-thiatriazinone 1, 1-dioxides were produced, which are heterocycles containing a part of the Burgess reagent and the K -area of amidinoheteroles. Graphical Abstract: