A direct route to 6,6'-disubstituted-2,2'-bipyridines by double Diels-Alder/retro Diels-Alder reaction of 5,5'-bi-1,2,4-triazines.
نویسنده
چکیده
Inverse electron demand Diels-Alder reaction of functionalized 5,5'-bi-1,2,4- triazines with bicyclo[2.2.1]hepta-2,5-diene in boiling p-cymene leads to a range of 6,6'- disubstituted-2,2'-bipyridines in good yield.
منابع مشابه
Synthesis of unsymmetrical annulated 2,2'-bipyridine analogues with attached cycloalkene and piperidine rings via sequential Diels-Alder Reaction of 5,5'-bi-1,2,4-triazines.
Synthesis of bisfunctionalized unsymmetrical 2,2'-bipyridines 8 or their sulfonyl derivatives 12a,b are described. They were prepared via the Diels-Alder reaction of 1-methyl-4-pyrrolidin-1-yl-1,2,3,6-tetrahydropyridine (6) with 3,3'-bis(methyl- sulfanyl)-5,5'-bi-1,2,4-triazine (1). The reaction leads to the single cycloaddition product 7 which undergoes Diels-Alder reaction with cyclic enamine...
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Synthesis of 2,3- and 3,4-cyclopentenopyridines, 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydroisoquinolines from 1,2,4-triazine derivatives is reported. Introduction of an alpha-functionalized methyl substituent (e.g. arylsulphonyl, sulphonamide, sulphonic acid ester) into position 3- or 6- of triazines by vicarious nucleophilic substitution of hydrogen and subsequent alkylation with alky...
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Substituted 3,4-dihydro-1,8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels-Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electron-demand Diels-Alder react...
متن کاملSynthesis of 2,5-disubstituted octahydroquinolin-4-ones via anintramolecular hetero Diels-Alder reaction.
A route for the preparation of 2,5-disubstituted octahydroquinolin-4-ones, synthetic precursors of the decahydroquinoline-type toxins, is presented. The key steps are an asymmetric epoxidation and an intramolecular hetero Diels-Alder reaction between an activated diene and an imine. The presence of an allylic stereogenic center induces some selectivity and thus only two cycloadducts are obtaine...
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ورودعنوان ژورنال:
- Molecules
دوره 10 1 شماره
صفحات -
تاریخ انتشار 2005