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 2010(3): 520-523
DOI: 10.1055/s-0029-1217120
DOI: 10.1055/s-0029-1217120
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
One-Pot Condensation-Oxidation of Glyoxamide with 1,2-Diamines Providing Imidazolines and Benzimidazoles
Weitere Informationen
Received
7 September 2009
Publikationsdatum:
13. November 2009 (online)
Publikationsverlauf
Publikationsdatum:
13. November 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/201003/lookinside/thumbnails/10.1055-s-0029-1217120-1.jpg)
Abstract
A novel method for the preparation of imidazolines and benzimidazoles bearing an amide at the 2-position, is described. The reactions of the glyoxamide with aliphatic and aromatic 1,2-diamines were found to form five-membered imidazolines and benzimidazoles by a one-pot condensation-oxidation procedure.
Key words
imidazolines - benzimidazolines - one-pot reaction - oxidations - amide
- For recent examples, see:
-
1a
Curini M.Epifano F.Montanari F.Rosati O.Taccone S. Synlett 2004, 1832 -
1b
Lin S.Yang L. Tetrahedron Lett. 2005, 46: 4315 -
1c
Das B.Holla H.Srinivas Y. Tetrahedron Lett. 2007, 48: 61 -
1d
Bahrami K.Khodaei MM.Naali F. J. Org. Chem. 2008, 73: 6835 ; and references therein -
2a
Fujioka H.Murai K.Ohba Y.Hiramatsu A.Kita Y. Tetrahedron Lett. 2005, 46: 2197 -
2b
Fujioka H.Murai K.Kubo O.Ohba Y.Kita Y. Tetrahedron 2007, 63: 638 -
2c
Gogoi P.Konwar D. Tetrahedron Lett. 2006, 47: 79 -
2d
Ishihara M.Togo H. Synlett 2006, 227 -
2e
Sayama S. Synlett 2006, 1479 - For recent reviews, see:
-
3a
Crouch RD. Tetrahedron 2009, 65: 2387 -
3b
Liu H.Du D.-M. Adv. Synth. Catal. 2009, 351: 489 - 4
Murai K.Morishita M.Nakatani R.Kubo O.Fujioka H.Kita Y. J. Org. Chem. 2007, 72: 8947 - For examples, see:
-
5a
Nakahara T.Okamoto N.Suzuki K.Kanie O. Carbohydr. Res. 2008, 343: 1624 -
5b
Nakamura S.Hyodo K.Nakamura Y.Shibata N.Toru T. Adv. Synth. Catal. 2008, 350: 1443 - For examples, see:
-
6a
Valdez-Padilla D.Rodoríguez-Morales S.Hernández-Campos A.Hernández-Luis F.Yépez-Mulia L.Tapia-Contreras A.Castillo R. Bioorg. Med. Chem. 2009, 17: 1724 -
6b
Guo Q.Chandrasekhar J.Ihle D.Wustrow DJ.Chenard BL.Krause JE.Hutchison A.Alderman D.Cheng C.Cortight D.Broom D.Kershaw MT.Simmermacher-Mayer J.Peng Y.Hodgetts KJ. Bioorg. Med. Chem. Lett. 2008, 18: 5027 -
6c
Borza I.Kolok S.Gere A.Nagy J.Fodor L.Galgóczy K.Fetter J.Bertha F.Ágai B.Horváth C.Farkas S.Domány G. Bioorg. Med. Chem. Lett. 2006, 16: 4638 -
6d
Venable JD.Cai H.Chai W.Dvorak CA.Grice CA.Jablonowski JA.Shah CR.Kwok AK.Ly KS.Pio B.Wei J.Desai PJ.Jiang W.Nguyen S.Ling P.Wilson SJ.Dunford PJ.Thurmond RL.Lovenberg TW.Karlsson L.Carruthers NI.Edwards JP. J. Med. Chem. 2005, 48: 8289 -
6e
Terzioglu N.van Rijn RM.Bakker RA.De Esch IJP.Leurs R. Bioorg. Med. Chem. Lett. 2004, 14: 5251 -
6f
Orjales A.Alonso-Cires L.López-Tudanca P.Tapia I.Mosquera R.Labeaga L. Eur. J. Med. Chem. 1999, 34: 415 -
7a
Zychlinski AV.Ugi I. Heterocycles 1998, 49: 29 -
7b
Hulme C.Cherrier M.-P. Tetrahedron Lett. 1999, 40: 5295 -
8a
Wolf FJ.Pfister K.Beutel RH.Wilson RM.Robinson CA.Stevens JR. J. Am. Chem. Soc. 1949, 71: 6 -
8b
Kazimierczuk Z.Pfleiderer W. Liebigs Ann. Chem. 1982, 754 -
8c
Lumma WC.Hartman RD.Saari WS.Engelhardt EL.Lotti VJ.Stone CA. J. Med. Chem. 1981, 24: 93 -
8d
Chen P.Barrish JC.Iwanowicz E.Lin J.Bednarz MS.Chen B.-C. Tetrahedron Lett. 2001, 42: 4293 -
8e
He W.Myers MR.Hanney B.Spada AP.Bilder G.Galzcinski H.Amin D.Needle S.Page K.Jayyosi Z.Perrone M. Bioorg. Med. Chem. Lett. 2003, 13: 3097 -
8f
Doherty EM.Fotsch C.Bannon AW.Bo Y.Chen N.Dominguez C.Falsey J.G avva NR.Katon J.Nixey T.Ognyanov VI.Pettus L.Rzasa RM.Stec M.Surapaneni S.Tamir R.Zhu J.Treanor JJS.Norman MH. J. Med. Chem. 2007, 50: 3515 -
9a
Ohta A.Watanabe T.Akita Y.Yoshida M.Toda S.Akamatsu T.Ohno H.Suzuki A. J. Heterocycl. Chem. 1982, 19: 1061 -
9b
Raw SA.Wilfred CD.Taylor RJK. Org. Biomol. Chem. 2004, 2: 788 -
10a
Raw SA.Wilfred CD.Taylor RJK. Chem. Commun. 2003, 2286 -
10b
Darkins P.Groarke M.McKervey MA.Moncrieff HM.McCarthy N.Nieuwenhuyzen M. J. Chem. Soc., Perkin Trans. 1 2000, 381 - Substituents on the nitrogen are also important; less nucleophilic nitrogens tends to lead to the formation of five-membered rings, see:
-
11a
Schönberg A.Singer E.Eckert P. Chem. Ber. 1980, 113: 2823 -
11b
Asami M.Inoue S. Chem. Lett. 1991, 685 -
11c
O’Brien P.Warren S. Tetrahedron Lett. 1995, 36: 2681 -
11d
Pikul S.McDow Dunham KL.Almstead NG.De B.Natchus MG.Anastasio MV.McPhail SJ.Snider CE.Taiwo YO.Rydel T.Dunaway CM.Gu F.Mieling GE. J. Med. Chem. 1998, 41: 3568 - 12 Condensation of glyoxalic acid with
1,2-diamines are known to form five-membered 2-carboxy imidazolidines,
see:
Halland N.Hazell RG.Jørgensen KA. J. Org. Chem. 2002, 67: 8331 - 13 For oxidative decarboxylation of
2-carboxy imidazolidines by NBS to give 2H-imidazolines,
see:
Murai K.Morishita M.Nakatani R.Fujioka H.Kita Y. Chem. Commun. 2008, 4498 - 16
Chakrabarty M.Mukherji A.Mukherjee R.Arima S.Harigaya Y. Tetrahedron Lett. 2007, 48: 5239 -
17a
Petyuniun PA.Choudry AM. Khim. Geterotsikl. Soedin. 1982, 5: 684 -
17b
Yorovenko VN.Kosarev SA.Zavarzin IV.Krayushkin MM. Russ. Chem. Bull. 1999, 48: 749 -
17c
Sharma P.Kumar A.Mandloi A. Synth. Commun. 2003, 33: 373 -
18a
Stetter H.Skobel H. Chem. Ber. 1987, 120: 643 -
18b
Ping X.Lin W.Zou X. Synthesis 2002, 1017
References
Using two equivalents of NBS afforded complex mixtures.
15Other reagents, such as NCS, NIS, NaClO2, oxone, TBHP, MCPBA, H2O2, CAN, and TsOH afforded poor results.