COMPOSITION, SYNTHESIS, AND USE OF A NEW CLASS OF ISONITRILES
This invention relates to novel isonitriles, including arylthio isonitriles, and methods for their preparation. The isonitriles include a conjugated ring system. The structure is designed with the flexibility to have multiple substitution patterns. The isonitriles may be used in applications including, but not limited to, pharmaceutical compositions.
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Paragraph 0089-0091
(2015/09/23)
Arylthio-metal exchange of α-arylthioalkanenitriles
The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me 2CuLi to α-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.
Nath, Dinesh,Skilbeck, Melanie C.,Coldham, Iain,Fleming, Fraser F.
supporting information
p. 62 - 65
(2014/01/23)
ORTHO-LITHIATION OF 2-(BENZOTHIAZOL-2-YLTHIO)PYRIDINE. PREPARATION OF 2,3-DISUBSTITUTED PYRIDINES
2-(Benzothiazol-2-ylthio)pyridine undergoes lithiation exclusively at the 3-position.The products of reaction with electrophiles of the lithiated species undergo sulfide cleavage to give 3-substituted 2-alkylthiopyridines and/or 3-substituted pyridine-2-thiones.
Katritzky, Alan R.,Aurrecoechea, Jose M.,Miguel, Luis M. Vazquez de
p. 427 - 436
(2007/10/02)
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