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Synlett 2008(19): 3016-3020
DOI: 10.1055/s-0028-1087352
DOI: 10.1055/s-0028-1087352
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Three-Component, One-Pot Sequential Synthesis of 1,3-Disubstituted 5-Arylhydantoins
Further Information
Received
6 August 2008
Publication Date:
12 November 2008 (online)
Publication History
Publication Date:
12 November 2008 (online)
Abstract
Reaction of carbodiimides with α-Br(Cl)-aryl acetic acids produces N,N′-substituted 5-arylhydantoins under very mild conditions and high yields. When the carbodiimides are generated in situ by Staudinger reaction, the process becomes a one-pot, three-component sequential synthesis of libraries of differently substituted 5-arylhydantoins.
Key words
heterocycles - multicomponent reactions - combinatorial chemistry - carbodiimides - sequential synthesis
-
1a
Comprehensive Organic Synthesis
Vol.
1-9:
Trost BM.Fleming I. Pergamon Press; Oxford: 1991. -
1b
Encyclopedia
of Reagents for Organic Synthesis
Vol. 1-8:
Paquette LA. Wiley and Sons; New York: 1995. - For recent reviews, see:
-
2a
Tietze LF. Chem. Rev. 1996, 96: 115 -
2b
Denmark SE.Thorarensen A. Chem. Rev. 1996, 96: 137 -
2c
Winkler JD. Chem. Rev. 1996, 96: 167 -
2d
Ryu I.Sonoda N.Curran DP. Chem. Rev. 1996, 96: 177 -
2e
Parsons PJ.Penkett CS.Shell AJ. Chem. Rev. 1996, 96: 195 -
2f
Wang KK. Chem. Rev. 1996, 96: 207 -
2g
Padwa A.Weingarten MD. Chem. Rev. 1996, 96: 223 -
2h
Malacria M. Chem. Rev. 1996, 96: 289 -
2i
Molander GA.Harris CR. Chem. Rev. 1996, 96: 307 -
2j
Tietze LF.Beifuss U. Angew. Chem. Int. Ed. Engl. 1993, 32: 131 -
2k
Ho T.-L. Tandem Organic Reactions Wiley and Sons; New York: 1992. - For an overview of multicomponent reactions, see:
-
3a
Multicomponent
Reactions
Zhu J.Bienaymé H. Wiley-VCH; Weinheim: 2005. -
3b
Multicomponent Reactions, In Tetrahedron Symposium-in-Print No 114
Vol. 61:
Marek I. Elsevier; Amsterdam: 2005. p.11309-11519 - 4
Andraos J. Org. Process Res. Dev. 2005, 9: 149 - For recent reviews, see:
-
5a
Orru RVA.de Greef M. Synthesis 2003, 1471 -
5b
Balme G.Bossharth E.Monteiro N. Eur. J. Org. Chem. 2003, 4101 -
5c
Dömling A. Chem. Rev. 2006, 106: 17 -
6a
Brouillette WJ.Jestkov VP.Brown ML.Akhtar MS.DeLorey TM.Brown GB. J. Med. Chem. 1994, 37: 3298 -
6b
Matsugi K.Kageyama M.Nishimura K.Giles H.Shirasawa E. Eur. J. Pharm. 1995, 275: 245 -
6c
Osz E.Somsak L.Szilagyi L.Kovacs L.Docsa T.Toth B.Gergely P. Bioorg. Med. Chem. Lett. 1999, 9: 1385 -
6d
Schelkum RM.Yuen PW.Sperpa K.Meltzer LT.Wise LD. J. Med. Chem. 2000, 43: 1892 -
6e
Stilz HU.Guba W.Jablonka B.Just M.Klingler O.Konig W.Wehner V.Zoller G. J. Chem. Med. 2001, 44: 1158 -
7a
Yokozeki K.Kubota K. Agric. Biol. Chem. 1987, 51: 721 -
7b
Yamada H.Shimizu S. Biocatalysis in Organic Synthesis Tramper J., van der Plas H. C. Elsevier; Amsterdam: 1985. p.19 - 8
Matthews J.Rivero RA. J. Org. Chem. 1997, 62: 6090 - 9
Beller M.Eckert M.Moradi WA.Neumann H. Angew. Chem. Int. Ed. 1999, 38: 1454 -
10a
Volonterio A.Ramirez de Arellano C.Zanda M.
J. Org. Chem. 2005, 70: 2161 -
10b
Volonterio A.Zanda M. Org. Lett. 2007, 5: 841
References and Notes
The reaction was carried out in dioxane because carbodiimide 2f was insoluble in CH2Cl2.
12The lower yields obtained with N,N′-dialkylcarbodiimides in the three-component process are probably due to lower yields in the Staudinger reaction.