Ring Expansion of Thiazolidine and Nucleophilic Substitution in N-Acyl Derivatives of 6-Thia-3,8-diazabicyclo[3.2.1.]octan-2-one
| Autor: | J. J. Herak, M. Kovačević, B. Gašpert |
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| Jazyk: | angličtina |
| Rok vydání: | 1982 |
| Předmět: | |
| Zdroj: | Croatica Chemica Acta Volume 55 Issue 3 |
| ISSN: | 0011-1643 1334-417X |
| Popis: | Sažetak Reaction of N3, N8-diacyl 6-thia-3, 8-diazabicyclo/3.2. l./octan-2- -one (I) with PC15 or S02Cl2 gave 6-chloro substituted N2, N5-diacyl 7-thia-2, 5-diazabicyclo/2.2.2./octan-3-one (II). Treatment of II with water yielded the 6-hydroxy derivative (III) while reaction with methanol gave the 6-methoxy derivative (IV). Under the same reaction conditions the mono N8-acyl derivative (V) gave a mixture of 6-substituted 7-thia-2, 5-diazabicyclo/2.2.2./octan-3-one and 4- -su bsti tuted 6-thia-3, 8-diazabicyclo/3.2. l ./octan-2-one derivatives (XIV and XV ; VI and VII ; VIII and IX). It was proposed that ring expansion of thiazolidine and nucleophilic substitution occured vi a the thiiranium ion XIII as a common intermediate. |
| Databáze: | OpenAIRE |
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