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Synthesis 2005(1): 161-165
DOI: 10.1055/s-2004-831225
DOI: 10.1055/s-2004-831225
PSP
© Georg Thieme Verlag Stuttgart · New York
Synthesis of α-Isocyano-α-alkyl(aryl)acetamides and their Use in the Multicomponent Synthesis of 5-Aminooxazole, Pyrrolo[3,4-b]pyridin-5-one and 4,5,6,7-Tetrahydrofuro[2,3-c]pyridine
Further Information
Received
26 May 2004
Publication Date:
16 September 2004 (online)
Publication History
Publication Date:
16 September 2004 (online)
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Abstract
α-Isocyano-β-phenylpropionamide 1 is synthesized from the corresponding amino acid in excellent yield. The unique reactivity of this bifunctional compound is exploited for the development of novel multicomponent synthesis of 5-aminooxazole 6, pyrrolo[3,4-b]pyridin-5-one 10 and 4,5,6,7-tetrahydrofuro[2,3-c]pyridine 13.
Key words
domino process - multicomponent reaction - heterocycles - isonitrile - oxazole - pyrrolopyridinone - tetrahydrofuropyridine
- For recent reviews, see:
-
1a
Ikeda SI. Acc. Chem. Res. 2000, 33: 511 -
1b
Weber L. Curr. Med. Chem. 2002, 9: 2085 -
1c
Dömling A. Curr. Opin. Chem. Biol. 2002, 6: 306 -
1d
Hulme C.Gore V. Curr. Med. Chem. 2003, 10: 51 -
1e
Orru RVA.De Greef M. Synthesis 2003, 1471 -
1f
Balme G.Bossharth E.Monteiro N. Eur. J. Org. Chem. 2003, 4101 -
1g
Jacobi von Wangelin A.Neumann H.Gördes D.Klaus S.Strübing D.Beller M. Chem.-Eur. J. 2003, 9: 4286 -
1h
Murakami M. Angew. Chem. Int. Ed. 2003, 42: 718 -
2a
Zhu J. Eur. J. Org. Chem. 2003, 1133 -
2b
Dömling A.Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168 -
3a
Hoppe D. Angew. Chem., Int. Ed. Engl. 1974, 13: 789 -
3b
Schöllkopf U. Angew. Chem., Int. Ed. Engl. 1977, 16: 339 - 4
Van Leusen D.Van Leusen AM. Org. React. 2001, 57: 417 - 5
Marcaccini S.Torroba T. Org. Prep. Proced. Int. 1993, 25: 141 - 6
Sun X.Janvier P.Zhao G.Bienaymé H.Zhu J. Org. Lett. 2001, 3: 877 - 7
Janvier P.Sun X.Bienaymé H.Zhu J. J. Am. Chem. Soc. 2002, 124: 2560 - 8
Fayol A.Zhu J. Org. Lett. 2004, 6: 115 - 9
Zhao G.Bughin C.Bienaymé H.Zhu J. Synlett 2003, 1153 -
10a
Urban R.Marquarding D.Seidel P.Ugi I.Weinelt A. Chem. Ber. 1977, 110: 2012 -
10b
Nunami KI.Suzuki M.Matsumoto K.Yoneda N.Takiguchi K. Agric. Biol. Chem. 1984, 48: 1073 -
10c
Mazurkiewicz R. Synthesis 1992, 941 -
11a
Suzuki M.Nunami KI.Moriya T.Matsumoto K.Yoneda N. J. Org. Chem. 1978, 43: 4933 -
11b
Bon RS.Hong C.Bouma MJ.Schmitz RF.De Kanter FJJ.Lutz M.Spek AL.Orru RVA. Org. Lett. 2003, 5: 3759 -
12a
Kulkarni BA.Ganesan A. Tetrahedron Lett. 1999, 40: 5633 -
12b
Sisko J.Kassick AJ.Mellinger M.Filan JJ.Allen A.Olsen MA. J. Org. Chem. 2000, 65: 1516 ; and references cited therein -
13a
Zhao G.Sun X.Bienaymé H.Zhu J. J. Am. Chem. Soc. 2001, 123: 6700 -
13b
González-Zamora E.Fayol A.Bois-Choussy M.Chiaroni A.Zhu J. J. Chem. Soc., Chem. Commun. 2001, 1684 -
13c
Gámez-Montaño R.Zhu J. J. Chem. Soc., Chem. Commun. 2002, 2448 -
13d
Fayol A.Zhu J. Angew. Chem. Int. Ed. 2002, 41: 3633 -
13e
Janvier P.Bienaymé H.Zhu J. Angew. Chem. Int. Ed. 2002, 41: 4291 -
13f
Gámez-Montaño R.González-Zamora E.Potier P.Zhu J. Tetrahedron 2002, 58: 6351 -
13g
Janvier P.Bois-Choussy M.Bienaymé H.J . Angew. Chem. Int. Ed. 2003, 42: 811