2008
DOI: 10.1016/j.tetlet.2007.11.138
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Sequential homo-coupling Diels–Alder/retro Diels–Alder reaction of 5,5′-bi-1,2,4-triazine-containing thiamacrocycles as a new route to thiacrown ethers incorporating a 2,2′-bipyridine subunit

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Cited by 23 publications
(6 citation statements)
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“…[14] In this work, we report a new approach to 1:1 thiacrown ether macrocycles and their sulfoxides incorporating a cyclopenteno[c]2,2Ј-bipyridine subunit, as well as X-ray crystallographic analysis of the target ligands. Our preliminary findings [15] and these studies suggest that this approach is fairly general for the preparation of large-sized rings, that is, rings having 13-22 or more atoms.…”
Section: Introductionmentioning
confidence: 52%
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“…[14] In this work, we report a new approach to 1:1 thiacrown ether macrocycles and their sulfoxides incorporating a cyclopenteno[c]2,2Ј-bipyridine subunit, as well as X-ray crystallographic analysis of the target ligands. Our preliminary findings [15] and these studies suggest that this approach is fairly general for the preparation of large-sized rings, that is, rings having 13-22 or more atoms.…”
Section: Introductionmentioning
confidence: 52%
“…Bis(1,2,4-triazin-3-ylsulfanyl)-3,6-dioxaoctane (3a): Spectral data is described in a previous communication. [15] 1,11-Bis (1,2,4-trizin-3-ylsulfanyl) Bis(1,2,4-trizin-3-ylsulfanyl)-3,6,9 General Procedure for the Preparation of 5,5Ј-Bi-1,2,4-triazine-Containing Thiamacrocycles 4a-c and 10: A suspension of compound 3a-c or 9 (0.59 mmol) in water (134 mL) was stirred at 40°C until complete dissolution. After cooling to room temperature, potassium cyanide (0.137 g, 2.12 mmol) was added as a solid, and the resulting mixture was stirred for the period of time indicated in Table 1.…”
Section: General Procedures For the Preparation Of 124-triazine Sulfmentioning
confidence: 99%
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“…Syntheses of 1,8-bis(1,2,4-triazin-3-ylsulfanyl)-3,6-dioxaoctane 3a, 1,11-bis(1,2,4-triazin-3-ylsulfanyl)-3,6,9-trioxaundecane 3b, 1,14-bis(1,2,4-triazin-3-ylsulfanyl)-3,6,9,12-tetraoxatetradecane 3c, 4,7-dioxa-1,10-dithia [10]3,3′-5,5′-bis(1,2,4-triazin-3-ylsulfanyl)cyclophane 4a, 4,7,10-trioxa-1,13-dithia [13]3,3′-5,5′-bis(1,2,4-triazin-3-ylsulfanyl)cyclophane 4b, 4,7,10,13-tetraoxa-1,16-dithia [16]3,3′-5,5′-bis(1,2,4-triazin-3-ylsulfanyl)cyclophane 4c were performed according to our published procedures. 6,7 General procedure for the preparation of thiacrown ethers (5a-c) and (6a-b) Method A. A solution of 2,5-norbornadiene (1.8 ml) in p-cymene (4 ml) containing compounds 4a-b (0.59 mmol) was heated for 20-24 h (see Table 1) at 140 °C.…”
Section: Methodsmentioning
confidence: 99%
“…4 However, synthetic efforts in this area have been hampered by the lack of the efficient methods of their synthesis. 5 In our preliminary work 6 we have shown that 1,2,4-triazine bis-sulfides, tethered to poly(ethylene glycol) chains undergo a remarkably facile, intramolecular cyclization into previously unknown 5,5′-bi-1,2,4-triazine thiacrown ethers (Scheme 1). The latter undergo an inverse electron demand Diels-Alder/retro Diels-Alder (DArDA) reaction with electron rich dienophiles affording bpy, or annulated bpy thiacrown ethers.…”
Section: Introductionmentioning
confidence: 99%