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Synthesis and properties of novel macrocyclic compounds bearing thiourea moieties by use of chemical feature of hypervalent sulfur
Author(s) -
Matsumura Noboru,
Konishi Tsunao,
Hayashi Hirokazu,
Mizuno Kazuhiko,
Yasui Masanori,
Iwasaki Fujiko
Publication year - 2002
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.5570390128
Subject(s) - hypervalent molecule , chemistry , thiourea , moiety , sulfur , ring (chemistry) , hydrolysis , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , reagent
Macrocyclic compounds 5a‐i bearing two tetraazathiapentalene frameworks were synthesized by the reaction of 10‐S‐3 tetraazathiapentalene derivatives 3a‐f with compounds having various diisothiocyanate functions 4a‐e. The reduction of the macrocyclic compounds with NaBH 4 afforded the ring‐opened macrocyclic compounds 11a‐b and 11e‐h by elimination of the hypervalent sulfur. The structures of these compounds were established by their spectral data and also by the X‐ray crystallographic analysis of lla. The other ring‐opened macrocyclic compounds 14a and 14e‐h that bear four thiourea groups were synthesized by alkaline hydrolysis of 5a and 5e‐h in that elimination of the C=S IV moiety in the tetraazathiapentalene rings occurred.