RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2008(13): 2077-2082
DOI: 10.1055/s-2008-1067112
DOI: 10.1055/s-2008-1067112
PAPER
© Georg Thieme Verlag Stuttgart · New York
One-Pot Multicomponent Synthesis of N-Substituted Tryptophan-Derived Diketopiperazines
Weitere Informationen
Received
31 March 2008
Publikationsdatum:
21. Mai 2008 (online)
Publikationsverlauf
Publikationsdatum:
21. Mai 2008 (online)

Abstract
A simple, rapid, one-pot multicomponent synthesis of tryptophan-derived diketopiperazines with variable side chains is presented. Microwave radiation gives comparable yields, but allows a significant decrease in reaction times.
Key words
multicomponent reactions - heterocycles - diketopiperazines - dioxopiperazines - tryptophan - indole alkaloids
-
1a
Humphrey GR.Kuethe JT. Chem. Rev. 2006, 106: 2875 -
1b
Somei M.Yamada F. Nat. Prod. Rep. 2005, 22: 73 -
1c
Lounasmaa M.Tolvanen A. Nat. Prod. Rep. 2000, 17: 175 -
1d
Faulkner DJ. Nat. Prod. Rep. 1999, 16: 155 ; and references cited therein -
2a
Sanz-Cervera JF.Stocking EM.Usui T.Osada H.Williams RM. Bioorg. Med. Chem. 2000, 8: 2407 -
2b
Wang H.Usui T.Osada H.Ganesan A. J. Med. Chem. 2000, 43: 1577 -
2c
Zhao S.Smith KS.Deveau AM.Dieckhaus CM.Johnson MA.Macdonald TL.Cook JM. J. Med. Chem. 2002, 45: 1559 -
3a
Fischer PM. J. Pept. Sci. 2003, 9: 9 -
3b
Dinsmore CJ.Beshore DC. Tetrahedron 2002, 58: 3297 ; and references cited therein -
4a
Acharya AN.Ostresh JM.Houghten RA. J. Comb. Chem. 2001, 3: 612 -
4b
Grundmann A.Li SM. Microbiology 2005, 151: 2199 - 5
Wyatt PG.Allen MJ.Borthwick AD.Davies DE.Exall AM.Hatley RJD.Irving WR.Livermore DG.Miller ND.Nerozzi F.Sollis SL.Szardenings AK. Bioorg. Med. Chem. Lett. 2005, 15: 2579 -
6a
Dömling A. Chem. Rev. 2006, 106: 17 -
6b
Dömling A.Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168 -
6c
Multicomponent Reactions
Zhu J.Bienaymé H. Wiley-VCH; Weinheim: 2005. -
7a
Tempest P.Ma V.Thomas S.Hua Z.Kelly MG.Hulme C. Tetrahedron Lett. 2001, 42: 4959 -
7b
Banfi L.Basso A.Guanti G.Kielland N.Repetto C.Riva R. J. Org. Chem. 2007, 72: 2151 - 8
Pulici M.Cervi G.Martina K.Quartieri F. Comb. Chem. High Throughput Screening 2003, 6: 693 -
9a
Rivera DG.Wessjohann L. J. Am. Chem. Soc. 2006, 128: 7122 -
9b
Michalik D.Schaks A.Wessjohann LA. Eur. J. Org. Chem. 2007, 149 -
9c
de Greef M.Abeln S.Belkasmi K.Dömling A.Orru RVA.Wessjohann LA. Synthesis 2006, 3997 -
9d
Wessjohann LA.Rivera DG.León F. Org. Lett. 2007, 9: 4733 -
9e
Leon F.Rivera DG.Wessjohann LA. J. Org. Chem. 2008, 73: 1762 -
10a
Tierney PJ.Lidstrom P. Microwave Assisted Organic Synthesis Blackwell; Oxford: 2005. -
10b
Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250 -
10c
Microwaves in Organic Synthesis
Loupy A. Wiley-VCH; Weinheim: 2002. -
11a
Anshu D.Ruby S.Pritima S.Sarita K. Chin. J. Chem. 2006, 24: 950 -
11b
Tu S.Zhu X.Zhang J.Xu J.Zhang Y.Wang Q.Jia R.Jiang B.Zhang J.Yao C. Bioorg. Med. Chem. Lett. 2006, 16: 2925 -
11c
Gelens E.De Kanter FJJ.Schmitz RF.Sliedregt LAJM.Van Steen BJ.Kruse CG.Leurs R.Groen MB.Orru RVA. Mol. Diversity 2006, 10: 17 -
12a
Braga AL.Vargas F.Sehnem JA.Wessjohann LA. Eur. J. Org. Chem. 2006, 22: 4993 -
12b
Braga AL.Silveira CC.de Bolster MWG.Schrekker HS.Wessjohann LA.Schneider PH. J. Mol. Catal. A: Chem. 2005, 239: 235 -
12c
Braga AL.Paixão MW.Westermann B.Schneider PH.Wessjohann LA. J. Org. Chem. 2008, 73: 2879 - 13
Mumm O. Ber. Dtsch. Chem. Ges. 1910, 32: 3807