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Volumn , Issue 10, 2013, Pages 1849-1859

Off the beaten track: The use of secondary amines in the Ugi reaction

Author keywords

Molecular diversity; Multicomponent reactions; Nitrogen heterocycles; Rearrangement; Synthetic methods

Indexed keywords


EID: 84875477613     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201201660     Document Type: Review
Times cited : (49)

References (57)
  • 1
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    • For a nice account on the discovery of the Ugi reaction see.
    • For a nice account on the discovery of the Ugi reaction see:, A. Dömling, Heterocycles 2007, 73, 1-11.
    • (2007) Heterocycles , vol.73 , pp. 1-11
    • Dömling, A.1
  • 3
    • 0001605801 scopus 로고
    • Mannich and Passerini, to whom we owe the two best-known three component reactions, are the grandparents of the four-component condensation, the Ugi reaction. Its parents are Ugi and Steinbrückner, assisted by co-workers of that period. The godparents are Optiz and Merz, McFarland and Sjöberg", cited in: The Passerini and Ugi Reactions.
    • "Mannich and Passerini, to whom we owe the two best-known three component reactions, are the grandparents of the four-component condensation, the Ugi reaction. Its parents are Ugi and Steinbrückner, assisted by co-workers of that period. The godparents are Optiz and Merz, McFarland and Sjöberg", cited in: The Passerini and Ugi Reactions, I. Ugi, S. Lohberger, R. Karl, Comprehensive Org. Synthesis 1991, 2, 1083-1109.
    • (1991) Comprehensive Org. Synthesis , vol.2 , pp. 1083-1109
    • Ugi, I.1    Lohberger, S.2    Karl, R.3
  • 4
    • 84875428919 scopus 로고    scopus 로고
    • For exhaustive reviews on Ugi reactions, see
    • For exhaustive reviews on Ugi reactions, see
  • 5
    • 2542509173 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3168 - 3210.
    • A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300; Angew. Chem. Int. Ed. 2000, 39, 3168-3210.
    • (2000) Angew. Chem. , vol.112 , pp. 3300
    • Dömling, A.1    Ugi, I.2
  • 7
    • 0020211577 scopus 로고
    • Angew. Chem. Int. Ed. Engl. 1982, 21, 810 - 819.
    • I. Ugi, Angew. Chem. 1982, 94, 826; Angew. Chem. Int. Ed. Engl. 1982, 21, 810-819.
    • (1982) Angew. Chem. , vol.94 , pp. 826
    • Ugi, I.1
  • 9
    • 84875458187 scopus 로고    scopus 로고
    • For interesting reviews on post-transformation strategies see
    • For interesting reviews on post-transformation strategies see
  • 16
    • 84875470940 scopus 로고    scopus 로고
    • Intramolecular attack of the imino-anhydride intermediate, generated using a primary amine, by means of an hydroxy group, has been described in the reactions between α-amino acids, isocyanides, and glycolaldehyde dimer or homoserine, aldehydes, and isocyanides. In these cases the formation of the more stable six- and five-membered rings is favored instead of nitrogen-mediated transacylation to give the quite strained three-membered rings, see
    • Intramolecular attack of the imino-anhydride intermediate, generated using a primary amine, by means of an hydroxy group, has been described in the reactions between α-amino acids, isocyanides, and glycolaldehyde dimer or homoserine, aldehydes, and isocyanides. In these cases the formation of the more stable six- and five-membered rings is favored instead of nitrogen-mediated transacylation to give the quite strained three-membered rings, see
  • 19
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    • with α-amino acids the cyclic imino-anhydride intermediate is attacked by the solvent, see:, Angew. Chem. Int. Ed. Engl. 1996, 35, 173 - 175.
    • with α-amino acids the cyclic imino-anhydride intermediate is attacked by the solvent, see:, A. Demharter, W. Hörl, E. Herdtweck, I. Ugi, Angew. Chem. 1996, 108, 185; Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175.
    • (1996) Angew. Chem. , vol.108 , pp. 185
    • Demharter, A.1    Hörl, W.2    Herdtweck, E.3    Ugi, I.4
  • 21
    • 84875449926 scopus 로고
    • Isonitrile Chemistry (Ed.:, Academic Press, New York.
    • Isonitrile Chemistry (Ed.:, I. Ugi), Academic Press, New York, 1971.
    • (1971)
    • Ugi, I.1
  • 24
    • 84867051994 scopus 로고    scopus 로고
    • This observations were smartly exploited by Dömling in the synthesis of iminobisamides from α-amino acids, carbonyl compounds, isocyanides, and amines in methanol, see.
    • This observations were smartly exploited by Dömling in the synthesis of iminobisamides from α-amino acids, carbonyl compounds, isocyanides, and amines in methanol, see:, K. Khoury, M. K. Sinha, T. Nagashima, E. Herdtweck, A. Dömling, Angew. Chem. Int. Ed. 2012, 51, 10280-10283.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 10280-10283
    • Khoury, K.1    Sinha, M.K.2    Nagashima, T.3    Herdtweck, E.4    Dömling, A.5
  • 45
    • 84875450694 scopus 로고    scopus 로고
    • [3,4a,4b,9]
    • [3,4a,4b,9]
  • 46
    • 33947332030 scopus 로고
    • When an acid anhydride rearranges to another generalized acid anhydride, the latter is of less energy content than the former", cited from.
    • "When an acid anhydride rearranges to another generalized acid anhydride, the latter is of less energy content than the former", cited from:, C. D. Hurd, J. Chem. Educ. 1967, 44, 454-460.
    • (1967) J. Chem. Educ. , vol.44 , pp. 454-460
    • Hurd, C.D.1
  • 50
    • 70349130818 scopus 로고    scopus 로고
    • With thioacids instead of carboxylic acids the same reaction occurs at room temperature, see.
    • With thioacids instead of carboxylic acids the same reaction occurs at room temperature, see, Y. Rao, X. Li, S. J. Danishefsky, J. Am. Chem. Soc. 2009, 131, 12924-12926.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 12924-12926
    • Rao, Y.1    Li, X.2    Danishefsky, S.J.3
  • 51
    • 84875409609 scopus 로고    scopus 로고
    • 2,3-Diaminoindoles with this substitution pattern have not been reported in the literature
    • 2,3-Diaminoindoles with this substitution pattern have not been reported in the literature.
  • 56
    • 84875424654 scopus 로고    scopus 로고
    • US Patent 6927294- 2005.
    • US Patent 6927294- 2005.
  • 57
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    • The road not taken: a selection of Robert Frost's poems, Henry Holt and Company, LLC, New York, 2002.
    • The road not taken: a selection of Robert Frost's poems, Henry Holt and Company, LLC, New York, 2002.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.