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Arylboronic acid or boronate synthesis - Organic …
Earth-abundant and inexpensive titanium can catalyze alkyne iminoamination, which generates tautomers of 1,3-diimines. Upon treatment with base (DBU) and malononitrile, the multicomponent coupling product is converted to 2-amino-3-cyanopyridines in a one-pot procedure in good to modest yields. There is substantial control of regioselectivity for the substituents on the pyridine ring and on the 2-amino group. Several studies were done that provide significant evidence for a Dimroth rearrangement mechanism for 2-aminopyridine formation, including isolation of a 2-imino-1,2-dihydropyridine intermediate that undergoes rearrangement under the reaction conditions.
Synthesis of alkyl chlorides - Organic chemistry
The condensation of an enone or enal with cyanoacetamide derivatives and -BuOK furnishes either 3-cyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence of O2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from “decyanidative aromatization” of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkylcyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).