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Titolo:
Synthesis of diazadi(and tri)thiacrown ethers containing two 5-substituent(or 2-methyl)-8-hydroxyquinoline side arms
Autore:
Bradshaw, JS; Song, HC; Xue, GP; Bronson, RT; Chiara, JA; Krakowiak, KE; Savage, PB; Izatt, RM;
Indirizzi:
Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA Brigham YoungUniv Provo UT USA 84602 Chem & Biochem, Provo, UT 84602 USA Zhongshan Univ, Dept Chem, Guangzhou 510275, Peoples R China Zhongshan Univ Guangzhou Peoples R China 510275 510275, Peoples R China
Titolo Testata:
SUPRAMOLECULAR CHEMISTRY
fascicolo: 3, volume: 13, anno: 2001,
pagine: 499 - 508
SICI:
1061-0278(2001)13:3<499:SODTEC>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
MACRORING NITROGEN-ATOMS; EARTH METAL-IONS; CROWN-ETHERS; DIAZA-18-CROWN-6 LIGANDS; AZACROWN ETHERS; COMPLEXATION; UNITS; 8-HYDROXYQUINOLINE; CRYPTANDS; ANALOGS;
Keywords:
hydroxyquinoline; benzene; NMR spectrum; crown ethers;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
26
Recensione:
Indirizzi per estratti:
Indirizzo: Bradshaw, JS Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA Brigham Young Univ Provo UT USA 84602 m, Provo, UT 84602 USA
Citazione:
J.S. Bradshaw et al., "Synthesis of diazadi(and tri)thiacrown ethers containing two 5-substituent(or 2-methyl)-8-hydroxyquinoline side arms", SUPRAMOL CH, 13(3), 2001, pp. 499-508

Abstract

Sixteen new diazadi(or tri)thiacrown ethers containing two 5-substituent(or 2-methyl)-8-hydroxyquinolin-2-ylmethyl side arms have been prepared by a three-step process. First, the appropriate bis(alpha -chloroamide)s were treated with five dimercaptans in base to form macrocyclic di(or tri)thiadiamides. The macrocyclic diamides were reduced by BH3-THF to form 1,7-diaza-4-oxa-10,13-dithia-cyclopentadecane (11); 1,7-diaza-4,13-dioxa-10,16-dithiacyclooctadecane (12); 1,7-diaza-4-oxa-10, 13,16-trithiacyclooctadecane (13); 1,7-diaza-4,13,16-trioxa-10,19-dithiacycloheneicosane (14); and 1,10diaza-4,7-dioxa-13,16-dithiacyclooctadecane (15). The diazadi(or tri)thiacrown ethers were then treated with 8-hydroxyquinoline, 8-hydroxy-5methylquinoline, 5-chloro-8-hydroxyquinoline, and 8-hydroxy quinal dine in the presence of paraformaldelyde in refluxing benzene to form the bis(8-hydroxy-5-substituent(or 2-methyl)quinolin-7-ymethyl)-substituted diazadi(or tri)thiacrown ethers 16-31. The crown ethers containing two 8-hydroxyquinoline or 8-hydroxyquinaldine side arms proved to be mixtures of about 90% bis(8-hydroxyquinolin-7-ylmethyl)-substituted crown ethers; 9% mixed (8-hydroxyquinolin-7-ymethyl)-substituted and (8-hydroxyquinolin-5-ylmethyl)-substituted crown ethers;and 1% bis(S-hydroxyquinolin-5-ylmethyl)-substituted crown ethers.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 09/07/20 alle ore 15:23:00