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Synlett 2010(1): 153-157
DOI: 10.1055/s-0029-1218550
DOI: 10.1055/s-0029-1218550
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Four-Component Synthesis of Imidazolinium-Fused Heterocycles from Ugi-Smiles Couplings
Further Information
Received
8 October 2009
Publication Date:
14 December 2009 (online)
Publication History
Publication Date:
14 December 2009 (online)
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Abstract
New imidazolinium-fused scaffolds are synthesized via a one-pot, two-step procedure involving a Ugi-Smiles coupling of mercaptotriazine derivatives with an isocyanide, an aldehyde, and a primary amine.
Key words
triazine - mercaptan - Ugi-Smiles - multicomponent reaction - thioamide
-
1a
Jagodzinski TS. Chem. Rev. 2003, 103: 197 -
1b
Du W.Curran DP. Org. Lett. 2003, 5: 1765 -
1c
Narender M.Reddy MS.Sridhar R.Nageswar YVD.Rao KR. Tetrahedron Lett. 2005, 46: 5953 -
2a
Artis DR.Lipton MA. J. Am. Chem. Soc. 1998, 120: 12200 -
2b
Miwa JH.Patel AK.Vivatrat N.Popek SM.Meyer AM. Org. Lett. 2001, 3: 3373 -
2c
Bagley MC.Dale JW.Merritt EA.Xiong X. Chem. Rev. 2005, 105: 685 -
3a
Ozturk T.Ertas E.Mert O. Chem. Rev. 2007, 107: 5210 -
3b
Charette AB.Grenon M. J. Org. Chem. 2003, 68: 5792 -
3c
Zbruyev OI.Stiasni N.Kappe CO. J. Comb. Chem. 2003, 5: 145 -
4a
Dumestre P.El Kaim L.Grégoire A. Chem. Commun. 1999, 775 -
4b
Atlan V.El Kaim L.Grimaud L.Jana NK. Synlett 2002, 352 -
4c
El Kaim L.Grimaud L.Oble J. Angew. Chem. Int. Ed. 2005, 117: 7961 -
4d
El Kaim L.Grimaud L.Oble J. Org. Biomol. Chem. 2006, 4: 3410 -
4e
El Kaim L.Gizolme M.Grimaud L. Org. Lett. 2006, 8: 5021 -
4f
El Kaim L.Gageat M.Gaultier L. Synlett 2007, 500 -
4g
El Kaim L.Grimaud L.Coffinier D. Org. Lett. 2009, 11: 995 -
4h
El Kaim L.Grimaud L.Schiltz A. Org. Biomol. Chem. 2009, 7: 3024 -
4i
El Kaim L.Grimaud L. Mol. Divers. 2009, in press; DOI: 10.1007/s11030-009-9175-3 -
5a
El Kaim L.Gizolme M.Grimaud L.Oble J. Org. Lett. 2006, 8: 4019 -
5b
Barthelon A.Dos Santos A.El Kaim L.Grimaud L. Tetrahedron Lett. 2008, 49: 3208 -
5c
Barthelon A.El Kaim L.Gizolme M.Grimaud L. Eur. J. Org. Chem. 2008, 35: 5974 - 6
El Kaim L.Gizolme M.Grimaud L.Oble J. Synlett 2007, 465 - 7 For a related use of the Schollkopf
isocyanide with thiocarboxylic acid, see:
Heck S.Dömling A. Synlett 2000, 424 - 8
Daunis J.Jacquier R.Viallefont P. Bull. Soc. Chim. Fr. 1969, 10: 3675 - 9
Boger DL. Chem. Rev. 1986, 86: 781 - 10
Akritopoulou-Zanze I.Wang Y.Zhao H.Djuric SW. Tetrahedron Lett. 2009, in press; DOI: 10.1016/j.tetlet.2009.07.036 - For related cyclization of thioamides with the formation of fused nitrogen heterocycles, see:
-
12a
Shibahara F.Kitagawa A.Yamaguchi E.Murai T. Org. Lett. 2006, 8: 5621 -
12b
Shibahara F.Yoshida A.Murai T. Chem. Lett. 2008, 37: 646
References and Notes
The crystallographic data can be obtained free of charge under the reference CCDC 730687 at the Cambridge Crystallographic Data Centre (www.ccdc.cam.ac.uk/data_request_cif).