On the Intramolecular 1,4-Dipolar Cycloaddition Reaction of Thiazinium Betaines for the Construction of Aza-, Diaza-, and Polyaza HeterocyclicRing Systems
| dc.contributor.author | Padwa, A.; | en |
| dc.contributor.author | Coats, S.J.; | en |
| dc.contributor.author | Harring, S.R.; | en |
| dc.contributor.author | Hadjiarapoglou, L.; | en |
| dc.contributor.author | Semones, A. | en |
| dc.date.accessioned | 2015-11-24T16:43:11Z | |
| dc.date.available | 2015-11-24T16:43:11Z | |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/8663 | |
| dc.rights | Default Licence | - |
| dc.subject | intramolecular - dipolar-cycloaddition - 1,4-dipole - heteroaromatic - cross-conjugated - betaine - 1,3-thiazinium hydroxide - S,S-ketene acetal - thioamide - cyclization | en |
| dc.title | On the Intramolecular 1,4-Dipolar Cycloaddition Reaction of Thiazinium Betaines for the Construction of Aza-, Diaza-, and Polyaza HeterocyclicRing Systems | en |
| heal.abstract | A series of bicyclic anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydroxides containing tethered Ο€-systems are easily prepared from the reaction of thiolactams with 1,3-bielectrophiles. These cross-conjugated heteroaromatic betaines undergo regio- and stereospecific 1,4-dipolar cycloaddition in good yield to produce cycloadducts containing a carbonyl sulfide bridge which can be induced to lose COS on further heating. Two of the cycloadducts were characterized by single crystal X-ray determinations. Control of ring size in the final product of the cycloaddition can be achieved by variation of the dipolarophilic chain length. Entry to the [6,6,5]- and [6,6,6]pyridone ring systems was possible using phenylalkynyl-substituted thioamides. Intramolecular 1,4-dipolar cycloaddition of a thiazinium betaine dipole also occurs across an indolyl Ο€-bond. With only one substituent group in the 9-position of the bicyclic betaine, the reaction takes an entirely different course unless a highly activated Ο€-bond is incorporated into the tether. The preferred reaction with modestly activated Ο€-systems corresponds to loss of the activated proton to produce an S,N-ketene acetal. When a ketene S,S-acetal group was incorporated onto the side chain, the 1,4-dipolar cycloaddition reaction was facilitated relative to proton loss. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | 10.1055/s-1995-4032 | - |
| heal.identifier.secondary | https://www.thieme-connect.com/ejournals/abstract/10.1055/s-1995-4032?locale=en&LgSwitch=1 | - |
| heal.journalName | Synthesis | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 1995 | - |
| heal.publisher | Georg Thieme Verlag | en |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |
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