- Synthesis of Alkynylthiopyridinium Salts and Their Use as Thioketene Equivalents
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A synthetic method has been developed for the preparation of dihalo(pyridinium)sulfuranes and their transformation into alkynylthiopyridinium salts, starting from inexpensive thiopyridones. The reactivity of these salts towards different nucleophiles is evaluated. Most thiols and amines are converted into dithioesters and thioamides, respectively; whereas sterically demanding thiols delivered alkynylthioethers. These results, together with preliminary mechanistic studies reveal that alkynylthiopyridinium salts can be considered synthetic equivalents of unstable thioketenes.
- Averesch, Kai F. G.,Pesch, Henner,Golz, Christopher,Alcarazo, Manuel
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- 1-dethia-2-thia-cephalosporanic acids
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1-dethia-2-thia-cephalosporanic acids of the formula STR1 wherein R is selected from the group consisting of STR2 Rb --NH--and STR3 Ra is an organic radical Ri and Rj are individually selected from the group consisting of hydrogen, aliphatic, aromatic and heterocycle or taken together with the nitrogen atom form an optionally substituted heterocycle, Rb is optionally substituted carbocyclic or heterocyclic aryl, R1B is --[CH=CH]n1 --CH2 --S--Rm, n1 is 0, 1 or 2, Rm is an unsaturated radical including a positively charged and doubly bonded nitrogen atom and bonded to the sulfur atom through a carbon atom, R4 is hydrogen or methoxy, n2 is 0, 1 or 2 and A is selected from the group consisting of hydrogen, alkali metal ion, or alkaline earth metal ion, magnesium ion, ammonium ion, an organic amine base and an ester group or --COOA is --COO- and their non-toxic, pharmaceutically acceptable acid addition salts, having antibiotic activity.
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