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Volumn 72, Issue 4, 2007, Pages 1526-1529

Intramolecular PIFA-mediated alkyne amidation and carboxylation reaction

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; CARBOXYLIC ACIDS; MOLECULAR DYNAMICS; PHASE TRANSITIONS;

EID: 33846982970     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062320s     Document Type: Article
Times cited : (103)

References (51)
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    • N-Methoxyamides and N-phthalimidoamides are also known to generate stable acyl-nitrenium intermediates. (a) Falvey, D. E.; Kung, A. C. J. Org. Chem. 2005, 70, 3127-3132.
    • N-Methoxyamides and N-phthalimidoamides are also known to generate stable acyl-nitrenium intermediates. (a) Falvey, D. E.; Kung, A. C. J. Org. Chem. 2005, 70, 3127-3132.
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    • It is known that terminal triple bonds react with PIFA to render α-hydroxyketones. Therefore, in our case, that position must be blocked for a successful transformation. Tamura, Y.; Yakura, T.; Haruta, J.-I.; Kita, Y. Tetrahedron Lett. 1985, 26, 3837-3840.
    • It is known that terminal triple bonds react with PIFA to render α-hydroxyketones. Therefore, in our case, that position must be blocked for a successful transformation. Tamura, Y.; Yakura, T.; Haruta, J.-I.; Kita, Y. Tetrahedron Lett. 1985, 26, 3837-3840.
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    • 3Al and the corresponding amine.
    • 3Al and the corresponding amine.
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    • For the preparation of carboxylic acid 3b, see: Arcadi, A.; Cacchi, S.; Delmastro, M.; Marinella, F. Synlett 1991, 409-411.
    • (b) For the preparation of carboxylic acid 3b, see: Arcadi, A.; Cacchi, S.; Delmastro, M.; Marinella, F. Synlett 1991, 409-411.
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    • For a recent review on amide bond formation, see
    • For a recent review on amide bond formation, see: Montalbetti, C. A. G. N.; Falque, V. Tetrahedron 2005, 61, 10827-10852.
    • (2005) Tetrahedron , vol.61 , pp. 10827-10852
    • Montalbetti, C.A.G.N.1    Falque, V.2
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    • The preparation and cyclization of amide 4a to afford pyrrolidinone 5a has already been performed see ref 1, It is included here for comparative purposes
    • The preparation and cyclization of amide 4a to afford pyrrolidinone 5a has already been performed (see ref 1). It is included here for comparative purposes.
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    • 2OH, was crucial for the success of the reaction. For a revision about the chemical properties and synthetic uses of trifluoroethanol and other related solvents, see: Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18-29.
    • 2OH, was crucial for the success of the reaction. For a revision about the chemical properties and synthetic uses of trifluoroethanol and other related solvents, see: Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18-29.
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    • It is noteworthy that the present access to 5-aroylpyrrolidines of type 5 offers many advantages over other alternatives described in the literature that involve multistep syntheses (chlorination plus Friedel-Craft acylation) starting from pyroglutamic acid or related derivatives, a process that lacks of regioselectivity when substituted arenes are employed. Rigo, B.; El Ghammarti, S.; Gautret, P.; Couturier, D. Synth. Commun. 1994, 24, 2597-2607.
    • (a) It is noteworthy that the present access to 5-aroylpyrrolidines of type 5 offers many advantages over other alternatives described in the literature that involve multistep syntheses (chlorination plus Friedel-Craft acylation) starting from pyroglutamic acid or related derivatives, a process that lacks of regioselectivity when substituted arenes are employed. Rigo, B.; El Ghammarti, S.; Gautret, P.; Couturier, D. Synth. Commun. 1994, 24, 2597-2607.
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    • It was additionally verified that the formation of a related pyrrolidine derivative by application of the cyclization conditions to N-methyl-4-pentenamide was not possible. Instead, a 5-hydroxymethyl-4,5- dihydrofuranone was the only identified product. Examples of this type of transformation can be found in: Takahata, H, Suzuki, T, Maruyama, M, Moriyama, K, Mozumi, M, Takamatsu, T, Yamazaki, T. Tetrahedron 1988, 44, 4777-4786
    • (b) It was additionally verified that the formation of a related pyrrolidine derivative by application of the cyclization conditions to N-methyl-4-pentenamide was not possible. Instead, a 5-hydroxymethyl-4,5- dihydrofuranone was the only identified product. Examples of this type of transformation can be found in: Takahata, H.; Suzuki, T.; Maruyama, M.; Moriyama, K.; Mozumi, M.; Takamatsu, T.; Yamazaki, T. Tetrahedron 1988, 44, 4777-4786.
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    • N-Alkylnitrenium ions would not be stable enough to exist.
    • N-Alkylnitrenium ions would not be stable enough to exist.
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    • Some selected examples of alkyne electrophilic cyclization employing oxygenated nucleophiles: (a) Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409-2412.
    • Some selected examples of alkyne electrophilic cyclization employing oxygenated nucleophiles: (a) Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409-2412.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.