dc.contributor.author | Christoforou, Irene C. | en |
dc.contributor.author | Koutentis, Panayiotis Andreas | en |
dc.creator | Christoforou, Irene C. | en |
dc.creator | Koutentis, Panayiotis Andreas | en |
dc.date.accessioned | 2019-11-21T06:17:20Z | |
dc.date.available | 2019-11-21T06:17:20Z | |
dc.date.issued | 2007 | |
dc.identifier.issn | 1477-0520 | |
dc.identifier.uri | http://gnosis.library.ucy.ac.cy/handle/7/55325 | |
dc.description.abstract | The regiocontrolled preparation of triarylisothiazoles is presented. 3-Halo-5-phenylisothiazole-4-carbonitriles, 1 (hal = Cl) and 18 (hal = I), are converted into the corresponding 4-bromo derivatives 5 (3-hal = Cl) and 24 (3-hal = I) via a Hunsdiecker strategy while the 4-iodo analogues 7 (3-hal = Cl) and 22 (3-hal = I) are prepared via a Hoffmann and Sandmeyer strategy. Regioselective Suzuki, Stille and Negishi reactions occur at C-4 with both the 4-bromo- and 4-iodoisothiazoles 5 and 7, the latter being more reactive than the former. 3-Iodoisothiazoles 22 and 24 fail to give regiocontrolled Suzuki, Stille or Negishi couplings, however, 4-bromo-3-iodo-5-phenylisothiazole 24 gives the regiospecific palladium catalysed Ullmann-type reaction product 3,3′-bi(4-bromo-5-phenylisothiazole) 25. Alkali hydrolysis of 3-chloro-4,5-diphenylisothiazole 8 gives the 3-hydroxy analogue 12 which is converted into 3-bromo-4,5-diphenylisothiazole 13 with POBr3. 3-Bromoisothiazole 13 reacts with phenylzinc chloride to give 3,4,5-triphenylisothiazole 17 but fails to undergo effective Suzuki or Stille couplings. 3,5-Diphenylisothiazole-4-carbonitrile 26 is converted into the 4-bromo- and 4-iodo-3,5-diphenylisothiazoles 30 and 34 both of which are effective for Suzuki and Stille couplings. A series of triarylisothiazoles are prepared in this manner and fully characterised. © The Royal Society of Chemistry. | en |
dc.source | Organic and Biomolecular Chemistry | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-34247562880&doi=10.1039%2fb702154b&partnerID=40&md5=28bef7241d95d380bf37c6fe96146ac6 | |
dc.subject | Synthesis (chemical) | en |
dc.subject | Bromine compounds | en |
dc.subject | Derivatives | en |
dc.subject | Hydrolysis | en |
dc.subject | 4-iodoisothiazoles | en |
dc.subject | Aromatic compounds | en |
dc.subject | Regiocontrolled synthesis | en |
dc.subject | Regioselectivity | en |
dc.subject | Triarylisothiazoles | en |
dc.title | 3,4,5-Triarylisothiazoles via C-C coupling chemistry | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1039/b702154b | |
dc.description.volume | 5 | |
dc.description.issue | 9 | |
dc.description.startingpage | 1381 | |
dc.description.endingpage | 1390 | |
dc.author.faculty | 002 Σχολή Θετικών και Εφαρμοσμένων Επιστημών / Faculty of Pure and Applied Sciences | |
dc.author.department | Τμήμα Χημείας / Department of Chemistry | |
dc.type.uhtype | Article | en |
dc.description.notes | <p>Cited By :14</p> | en |
dc.source.abbreviation | Org.Biomol.Chem. | en |
dc.contributor.orcid | Koutentis, Panayiotis Andreas [0000-0002-4652-7567] | |
dc.contributor.orcid | Christoforou, Irene C. [0000-0001-6624-3548] | |
dc.gnosis.orcid | 0000-0002-4652-7567 | |
dc.gnosis.orcid | 0000-0001-6624-3548 | |