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(5): 823-827
DOI: 10.1055/s-2007-990932
DOI: 10.1055/s-2007-990932
PSP
© Georg Thieme Verlag Stuttgart · New York
Direct Synthesis of Substituted Pyrimidines and Quinazolines
Weitere Informationen
Received
20 July 2007
Publikationsdatum:
28. November 2007 (online)
Publikationsverlauf
Publikationsdatum:
28. November 2007 (online)
Abstract
A variety of N-vinyl and N-aryl amides were converted in one step into the corresponding pyrimidine and quinazoline derivatives, respectively. Amide activation with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed by nitrile addition to the activated amide derivative and annulation provides the desired azaheterocycles.
Key words
amide - nitrile - pyrimidine - quinazoline - annulation
- Reviews:
-
1a
Undheim K.Benneche T. In Comprehensive Heterocyclic Chemistry II Vol. 6:Katritzky AR.Rees CW.Scriven EFV.McKillop A. Pergamon; Oxford: 1996. p.93 -
1b
Lagoja IM. Chem. Biodiversity 2005, 2: 1 -
1c
Michael JP. Nat. Prod. Rep. 2005, 22: 627 -
1d
Joule JA.Mills K. In Heterocyclic Chemistry Blackwell Science Ltd.; Cambridge MA: 2000. 4th ed.. p.194 -
1e
Erian AW. Chem. Rev. 1993, 93: 1991 - For representative reports, see:
-
2a
Sakai N.Youichi A.Sasada T.Konakahara T. Org. Lett. 2005, 7: 4705 -
2b
Yoon DS.Han Y.Stark TM.Haber JC.Gregg BT.Stankovich SB. Org. Lett. 2004, 6: 4775 -
2c
Kakiya H.Yagi K.Shinokubo H.Oshima K. J. Am. Chem. Soc. 2002, 124: 9032 -
2d
Kotsuki H.Sakai H.Morimoto H.Suenaga H. Synlett 1999, 1993 -
2e
Ghosez L.Jnoff E.Bayard P.Sainte F.Beaudegnies R. Tetrahedron 1999, 55: 3387 -
2f
Martínez AG.Fernández AH.Fraile AG.Subramanian LR.Hanack M. J. Org. Chem. 1992, 57: 1627 - For reviews, see:
-
3a
Chinchilla R.Nájera C.Yus M. Chem. Rev. 2004, 104: 2667 -
3b
Turck A.Plé N.Mongin F.Quéguiner G. Tetrahedron 2001, 57: 4489 - 4
Movassaghi M.Hill MD. J. Am. Chem. Soc. 2006, 128: 14254 - Reviews:
-
5a
Muci AR.Buchwald SL. Top. Curr. Chem. 2002, 219: 131 -
5b
Hartwig JF. In Handbook of Organopalladium Chemistry for Organic SynthesisNegishi E. Wiley-Interscience; New York: 2002. p.1051 -
5c
Beletskaya IP.Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337 -
5d
Dehli JR.Legros J.Bolm C. Chem. Commun. 2005, 973 -
6a
Movassaghi M.Hill MD. J. Am. Chem. Soc. 2006, 128: 4592 -
6b
Hill MD.Movassaghi M. Synthesis 2007, 1115 -
7a
Zielinski W.Kudelko A. Monatsh. Chem. 2000, 131: 895 -
7b
Kofanov ER.Sosnina VV.Danilova AS.Korolev PV. Zh. Prik. Khim. 1999, 72: 813 ; Russ. J. Appl. Chem. 1999, 72, 850 -
7c
Madroñero R.Vega S. Synthesis 1987, 628 - 8
Bose DS.Jayalakshmi B. Synthesis 1999, 64 - 9 For a review, see:
Baraznenok IL.Nenajdenko VG.Balenkova ES. Tetrahedron 2000, 56: 3077 -
10a
Charette AB.Grenon M. Can. J. Chem. 2001, 79: 1694 -
10b
Charette AB.Mathieu S.Martel J. Org. Lett. 2005, 7: 5401 -
11a
Myers AG.Tom NJ.Fraley ME.Cohen SB.Madar DJ. J. Am. Chem. Soc. 1997, 119: 6072 -
11b
Garcia BA.Gin DY. J. Am. Chem. Soc. 2000, 122: 4269