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Synthesis and properties of new macrocyclic compounds: Utilization of bond character of hypervalent sulfur in tetraazathiapentalene derivatives
Author(s) -
Matsumura Noboru,
Hirase Ryuji,
Kamitani Shigeki,
Okumura Yasuyuki,
Mizuno Kazuhiko
Publication year - 2005
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.5570420621
Subject(s) - hypervalent molecule , chemistry , sulfur , ring (chemistry) , indene , medicinal chemistry , organic chemistry , reagent
2,3‐Bis[( p ‐isothiocyanatomethylphenyl)methyl]‐6,7‐dihydro‐5 H ‐2a‐thia(2a‐S IV )‐2,3,4a,7a‐tetraaza‐cyclopent[ cd ]indene‐1,4(2 H ,3 H )‐dithione ( 3 ), prepared by the reaction of 2,3‐dimethyl‐6,7‐dihydro‐5 H ‐2a‐thia(2a‐S IV )‐2,3,4a,7a‐tetraazacyclopent‐[ cd ]indene‐1,4(2 H ,3 H )‐dithione ( 1 ) with p ‐xylylene diisothio‐cyanate, reacted with N,N′‐dialkyl substituted diamines to give macrocyclic compounds bearing hypervalent sulfur by a ring closure reaction in good yields. These macrocyclic compounds were converted into ring‐expanded macrocyclic compounds with release of the hypervalent sulfur by treating with NaBH 4 and CF 3 COOH.