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ChemInform Abstract: Electrophilic Cyanations. Part 1. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p- Toluenesulfonyl Cyanide.

โœ Scribed by A. MIYASHITA; I. NAGASAKI; A. KAWANO; Y. SUZUKI; K. IWAMOTO; T. HIGASHINO

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
28
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide. -A variety of mercapto-substituted heteroarenes (I) (15 examples) undergo electrophilic cyanation with tosyl cyanide (II) in THF to yield the thiocyanato derivatives (III). In DMF the tosylheteroarenes ( IV) are obtained. Using BrCN for electrophilic cyanation gives symmetrical disulfides as side products. Furthermore, electrophilic cyanation of the quinazolinone (VI) gives the N-substituted product ( VII) and 2-mercaptoaniline (VIII) yields the benzothiazole (IX) via cyclization of the primary 2-thiocyanatoaniline. -(MIYASHITA, A.; NAGASAKI, I.;

๐Ÿ“œ SIMILAR VOLUMES

ChemInform Abstract: Electrophilic Cyana
ChemInform Abstract: Electrophilic Cyanations. Part 2. Synthesis of Heteroarenecarbonitriles by Electrophilic Cyanation: Reaction of Metalated Heteroarenes with p-Toluenesulfonyl Cyanide.
โœ I. NAGASAKI; Y. SUZUKI; K. IWAMOTO; T. HIGASHINO; A. MIYASHITA ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 30 KB ๐Ÿ‘ 1 views

Electrophilic Cyanations. Part 2. Synthesis of Heteroarenecarbonitriles by Electrophilic Cyanation: Reaction of Metalated Heteroarenes with p-Toluenesulfonyl Cyanide. -Carefull regioselective lithiation of hetarenes or even arenes (I) followed by addition of Tos-CN gives fair yields of (hetero)aren