Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(16): 2767-2770
DOI: 10.1055/s-0030-1258139
DOI: 10.1055/s-0030-1258139
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
An Efficient Synthesis of Fused 3-Formylpyridines and 5-Formylpyrimidines
Further Information
Received
13 April 2010
Publication Date:
01 July 2010 (online)
Publication History
Publication Date:
01 July 2010 (online)

Abstract
Cyclization of 2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate with various amino heterocycles led to the formation of a series of fused heterocyclic systems containing a 3-formylpyridine or 5-formylpyrimidine unit.
Key words
fused pyridines - fused pyrimidines - cyclization reactions - amino heterocycles - 2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate
-
1a
Yan H.Boehm JC.Jin Q.Kasparec J.Li H.Zhu C.Widdowson KL.Callahan JF.Wan Z. Tetrahedron Lett. 2007, 48: 1205 -
1b
Bennett LR.Blankley CJ.Fleming RW.Smith RD.Tessman DK. J. Med. Chem. 1981, 24: 382 -
1c
Angiolini M.Bassini DF.Gude M.Menichincheri M. Tetrahedron Lett. 2005, 46: 8749 -
1d
Vanlaer S.Compernolle F.Voet A.Gielens C.De Maeyer M. Eur. J. Org. Chem. 2009, 643 -
1e
Wong A.Kuethe JT.Davies IW.Hughes DL. J. Org. Chem. 2004, 69: 7761 -
2a
Nishikawa Y.Shindo T.Ishii K.Nakamura H.Kon T.Uno H. J. Med. Chem. 1989, 32: 583 -
2b
Bleloch A.Johnson BFG.Ley SV.Price AJ.Shephard DS.Thomas AW. Chem. Commun. 1999, 1907 -
2c
Pham V.Zhang W.Chen V.Whitney T.Yao J.Froese D.Friesen AD.Diakur JM.Haque W. J. Med. Chem. 2003, 46: 3680 -
2d
VanderWel SN.Harvey PJ.McNamara DJ.Repine JT.Keller PR.Quin J.Booth RJ.Elliott WL.Dobrusin EM.Fry DW.Toogood PL. J. Med. Chem. 2005, 48: 2371 -
2e
Stuart A.Paterson T.Roth B.Aig E. J. Med. Chem. 1983, 26: 667 -
3a
Gupton JT.Gall JE.Riesinger SW.Smith SQ.Bevirt KM.Sikorski JA.Dahl ML.Arnold A.
J. Heterocycl. Chem. 1991, 28: 1281 -
3b
Ragan JA.McDermott RE.Jones BP.Ende DJ.Clifford PJ.McHardy SJ.Heck SD.Liras S.Segelstein BE. Synlett 2000, 1172 - 4
Tom NJ.Ruel EM. Synthesis 2001, 1351 - For the reactions of vinamidinium salts 1 and 2, see:
-
5a
Jameleddine K.Adnen HAM.Bechir BH. Tetrahedron Lett. 2006, 47: 2973 -
5b
Thouraya G.Jameleddine K.Adnen HAM.Bechir BH. Synth. Commun. 2007, 37: 1053 -
5c
Gupton JT.Krolikowski DA.Yu RH.Riesinger SW. J. Org. Chem. 1990, 55: 4735 -
5d
Angus RO.Bryce MR.Keshavarz B.Wudl F. Synthesis 1998, 746