Premium
Preparation and some reactions of 3,5:8,10‐di‐1,3‐benzo[8](3,4)‐1,2,5‐thiadiazolocyclophane
Author(s) -
Hatta Taizo,
Mataka Shuntaro,
Tashiro Masashi,
Suzuki Hiroshi,
Numano Katsutoshi
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280214
Subject(s) - chemistry , cyclophane , acetic anhydride , reagent , medicinal chemistry , sodium hydride , sodium sulfide , hydride , lithium (medication) , sulfide , sodium , aluminum hydride , pyrene , organic chemistry , metal , catalysis , crystal structure , medicine , methoxide , endocrinology
Titled 1,2,5‐thiadiazolometacyclophane 1 was prepared via thia[2.3]cyclophane 5 which was obtained by the reaction of di(bromomethyl) 2 with sodium sulfide under phase‐transfer‐catalyzed conditions. Cyclophane 1 gave the corresponding pyrene derivatives by the oxidative transannular reaction in the reaction with brominating reagent. Reduction of 1 with lithium aluminum hydride followed by acetylation with acetic anhydride gave a 4:l‐mixture of cis ‐ and trans ‐diamide 11 and 12 with a trace amount of cyclophane‐ring‐cleaved product 13 . On the other hand, 13 was obtained as a major product in the reduction with metal sodium and diisobutylaluminum hydride.