Electrophilic Cyanations. I. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide

Electrophilic Cyanations Using 1-Cyanobenzotriazole: sp2 and sp Carbanions

“…While this transformation is usually accomplished through the nucleophilic attack of a cyanide ion (CN - ) at an electrophilic carbon, a few reagents react as a cyano cation (CN + ) equivalent upon treatment with a carbanion. These include tosyl cyanide, − 2-chlorobenzylthiocyanate, and cyanogen chloride . Recently, we described a new and convenient synthesis of 1-cyanobenzotriazole ( 1 ) and preliminary results showing its utility as an electrophilic C-cyanating reagent by the conversion of arylacetonitrile anions to the corresponding aryl malononitriles (Scheme ).…”

Photodegradation of 2‐mercaptobenzothiazole disulfide and related benzothiazoles

“…Therefore the identification of the compound 7 is tentative. There are documented cases in which certain 13 C signals are not directly observable and are undetectable [7,8]. Further supporting information for the existence of a 2,x'-thiobisbenzothiazole are the publications by Cole et al [9] and Crank and Mursyidi [10].…”

“…In the case of the assignment of an unsymmetrical 2,x'-thiobisbenzothiazole (7) (where x = 4, 5, 6, 7 and refers to the position on the benzothiazole ring) an authentic standard or the starting material for its synthesis was not available, nor was there a spectrum in the computer databases or the literature. Although the high resolution mass spectra and the fragmentation pattern together with 1 H NMR support the proposed structure, the 13 C NMR spectrum lacks carbons in the positions 2 and 2'. Both carbons are quaternary and are part of the thiazole ring.…”

“…The changes in the UV spectra were measured using Cary 3 UV-Vis spectrophotometer (Varian Inc.) using 1 cm quartz cells. 1 H and 13 C NMR data were recorded on a Varian MercuryPlus-400 spectrometer (Varian Inc., Palo Alto, CA).…”

Rapid Synthesis of CDP840 with 2-Pyrimidyl Vinyl Sulfide as a Platform

“…Several syntheses of CDP840 including both racemic and asymmetric approaches were reported so far. , However, they suffered from a relatively long procedure (6−7 steps). We envisaged that the sequence of double Mizoroki−Heck-type arylation and cross-coupling starting from 2-pyrimidyl vinyl sulfide ( 2 ) , followed by hydrogenation of the CC bond would afford CDP840 ( 1 ) very rapidly (Scheme ). Such a synthesis would offer an opportunity for diversity-oriented synthesis, which would enable the production and screening of a series of CDP840-type triarylethanes.…”