The Synthesis of Analogs of Penicillin.^1a I

Reactions of Thiols with Sulfoxides. III. Catalysis by Acids and Bases

“…pyridine, which is both a weak acid and a weak base. 6 The results of this study are summarized in Table VI. As the thiol-2-hydroxypyridine ratio was varied from 50 to 10, the rate of oxidation increased by a factor of 7.5. Further, as shown in Figure 6, 2-hydroxypyridine is also a true catalyst for these reactions.…”

Azomethine Chemistry. IV. Chemistry of Fused Thiazolidines1,2

“…In connection with another study concerned with nucleophilic additions to azomethines,4 5the reaction of several /3-aminoethylmercaptans with yarious keto acids were of interest. Reactions of this type are well known and have been shown to provide saturated thiazolo [2,3-o]isoindoles,6 thiazolo[3,2-o]pyridines,6 and thiazolo [2,l-5]pyrroles.7 The present report concerns the preparation of several hexahydropyrrolo [2,[1][2][3][4][5][6]-thiazoles8 and a study of their chemical reactions and n.m.r. spectra.…”

“…109-110°; n.m.r. spectrum, r 2.68 m (5), 5.65 m (1), 6.38 m (1), and 2,2-Dimethyl-7a-phenyl-5-oxotetrahydropyrrolo [2,[1][2][3][4][5][6] thiazole (2b).-A solution of 3.56 g. (0.020 mole) of ß-benzoylpropionic acid, 2.82 g. (0.020 mole) of 2-mercapto-2-methylpropylamine hydrochloride, and 2.80 ml. (0.020 mole) of triethylamine in 220 ml.…”