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Akhil K Sahoo - One of the best experts on this subject based on the ideXlab platform.
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3 2 cycloaddition of nonstabilized azomethine ylides 7 stereoselective synthesis of epibatidine and analogues
Journal of Organic Chemistry, 1998Co-Authors: Ganesh Pandey, Trusar D Bagul, Akhil K SahooAbstract:Epibatidine (1) is synthesized by employing a [3 + 2] cycloaddition strategy as a key step via nonstabilized azomethine ylide 10, generated by one-electron oxidative double desilylation of N-benzyl-2,5-bis(trimethylsilyl)pyrrolidine (12). Cycloaddition of 10 with trans-ethyl-3-(6-chloro-3-pyridyl)-2-propenoate (22a) gives 26 in which the 6-chloro-3-pyridyl moiety is endo-oriented. Decarboxylation followed by debenzylation gives unnatural epimer 30 of 1. The required cycloadduct 33, in which 6-chloro-3-pyridyl moiety is exo-oriented, is obtained stereoselectively utilizing cis-ethyl-(6-chloro-3-pyridyl)-2-propenoate (22b) as dipolarophile. 30 is also converted to 1 by epimerization reaction using KOtBu. An alternative route involving conjugate addition of 6-chloro-3-iodo pyridine (37) to 36, obtained by cycloaddition of 10 with ethyl propiolate, is also suggested for the stereoselective synthesis of 1. A number of substituted epibatidines (38, 39, 40, 41, and 42) are synthesized through this strategy using...
A V Varlamov - One of the best experts on this subject based on the ideXlab platform.
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transformations of 2 trifluoroacetyl 4 5 6 7 tetrahydro 1h pyrrolo 3 2 c pyridines by the action of ethyl Propynoate a novel synthesis of 2 trifluoroacetyl 4 7 8 9 tetrahydro 1h pyrrolo 2 3 d azocines
Russian Journal of Organic Chemistry, 2006Co-Authors: L G Voskresenskii, T N Borisova, T A Vorobeva, O V Grishachkina, L N Kulikova, A I Chernyshev, A V VarlamovAbstract:2-Trifluoroacetyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridines reacted with ethyl Propynoate in acetonitrile and methanol to give ethyl 2-trifluoroaceyl-4,7,8,9-tetrahydro-1H-pyrrolo[2,3-d]azocine-5-carboxylates. The reactions of 2-trifluoroacetyl-1-vinyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridines with ethyl Propynoate in alcohols were accompanied by cleavage of the tetrahydropyridine fragment with formation of alkyl 3-{benzyl[2-(3-alkoxy-5-trifluoroacetyl-1-vinyl-1H-pyrrol-2-yl)ethyl]amino}acrylates.
Varlamov A.v. - One of the best experts on this subject based on the ideXlab platform.
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Transformations of 2-trifluoroacetyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c] pyridines by the action of ethyl Propynoate. A novel synthesis of 2-trifluoroacetyl-4,7,8,9-tetrahydro-1H-pyrrolo[2,3-d]azocines
'Pleiades Publishing Ltd', 2020Co-Authors: Voskresenskii L.g., Borisova T.n., Vorob'eva T.a., Grishachkina O.v., Kulikova L.n., Chernyshev A.i., Varlamov A.v.Abstract:2-Trifluoroacetyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridines reacted with ethyl Propynoate in acetonitrile and methanol to give ethyl 2-trifluoroaceyl-4,7,8,9-tetrahydro-1H-pyrrolo[2,3-d]azocine-5-carboxylates. The reactions of 2-trifluoroacetyl-1-vinyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c] pyridines with ethyl Propynoate in alcohols were accompanied by cleavage of the tetrahydropyridine fragment with formation of alkyl 3-{benzyl[2-(3-alkoxy-5- trifluoroacetyl-1-vinyl-1H-pyrrol-2-yl)ethyl]amino}acrylates. © 2006 Pleiades Publishing, Inc
Ganesh Pandey - One of the best experts on this subject based on the ideXlab platform.
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3 2 cycloaddition of nonstabilized azomethine ylides 7 stereoselective synthesis of epibatidine and analogues
Journal of Organic Chemistry, 1998Co-Authors: Ganesh Pandey, Trusar D Bagul, Akhil K SahooAbstract:Epibatidine (1) is synthesized by employing a [3 + 2] cycloaddition strategy as a key step via nonstabilized azomethine ylide 10, generated by one-electron oxidative double desilylation of N-benzyl-2,5-bis(trimethylsilyl)pyrrolidine (12). Cycloaddition of 10 with trans-ethyl-3-(6-chloro-3-pyridyl)-2-propenoate (22a) gives 26 in which the 6-chloro-3-pyridyl moiety is endo-oriented. Decarboxylation followed by debenzylation gives unnatural epimer 30 of 1. The required cycloadduct 33, in which 6-chloro-3-pyridyl moiety is exo-oriented, is obtained stereoselectively utilizing cis-ethyl-(6-chloro-3-pyridyl)-2-propenoate (22b) as dipolarophile. 30 is also converted to 1 by epimerization reaction using KOtBu. An alternative route involving conjugate addition of 6-chloro-3-iodo pyridine (37) to 36, obtained by cycloaddition of 10 with ethyl propiolate, is also suggested for the stereoselective synthesis of 1. A number of substituted epibatidines (38, 39, 40, 41, and 42) are synthesized through this strategy using...
Niyum Ramesar - One of the best experts on this subject based on the ideXlab platform.
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a novel tetrahydrofuran derivative via a tertiary ketol type rearrangement
Tetrahedron Letters, 1993Co-Authors: Siegfried E Drewes, John S. Field, Neville D Emslie, A A Khan, Niyum RamesarAbstract:Abstract Hexahydro-3a, 7a-dihydroxy-3,7,7-trimethyl-2-phenyl-4H-furo [3,2-c]pyran-4-one 6 has been obtained from the reaction between tetrahydro-4, 4-dimethyl-2-oxo-3-furanyl propanoate 4 , benzaldehyde and base. The product is the result of a modified benzilic acid rearrangement.
