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 2008(7): 1069-1077
DOI: 10.1055/s-2008-1066988
DOI: 10.1055/s-2008-1066988
PAPER
© Georg Thieme Verlag Stuttgart · New York
A New One-Step Route for the Synthesis of Fused Pyrido[1,2-a]pyrimidin-4-ones
Further Information
Received
20 November 2007
Publication Date:
06 March 2008 (online)
Publication History
Publication Date:
06 March 2008 (online)

Abstract
The cyclization of 3-formylchromone with a variety of 2-methylpyrimidin-4(3H)-ones promoted by chlorotrimethylsilane was investigated. A simple and flexible general procedure for the synthesis of a series of fused pyrido[1,2-a]pyrimidin-4-ones is proposed. A set of functionally and structurally diverse pyrido[1,2-a]pyrimidin-4-ones were obtained in high yields.
Key words
3-formylchromone - 2-methylpyrimidin-4(3H)-ones - fused-ring systems - cyclizations - chlorotrimethylsilane
-
1a
Tilley JW.Burghardt B.Burghardt C.Mowles TF.Leinweber F.-J.Klevans L.Young R.Hirkaler G.Fahrenholtz K.Zawoiski S.Todaro LJ. J. Med. Chem. 1988, 31: 466 -
1b
Tilley JW.Levitan P.Lind J.Welton AF.Crowley HJ.Tobias LD.O’Donnell M. J. Med. Chem. 1987, 30: 185 -
1c
Tilley JW.Levitan P.Welton AF.Crowley HJ. J. Med. Chem. 1983, 26: 1638 -
1d
Schwender CF.Sunday BR.Decker VL. J. Med. Chem. 1982, 25: 742 -
1e
Tilley JW.LeMahieu RA.Carson M.Kierstead RW.Baruth HW.Yaremko B. J. Med. Chem. 1980, 23: 92 -
1f
Schwender CF.Sunday BR.Herzig DJ.Kusner EK.Schumann PR.Gawlak DL. J. Med. Chem. 1979, 22: 748 -
1g
Schwender CF.Sunday BR.Herzig DJ. J. Med. Chem. 1979, 22: 114 -
2a
Biere H, andKapp J.-F. inventors; DE 2739020. ; Chem. Abstr. 1979, 90, 204131 -
2b
Kierstead RW, andTilley JW. inventors; DE 2812586. ; Chem. Abstr. 1979, 90, 38953 -
2c
Kierstead RW, andTilley JW. inventors; DE 2812585. ; Chem. Abstr. 1979, 90, 87500 -
2d
Schwender CF, andSunday BR. inventors; US 4066767. ; Chem. Abstr. 1978, 88, 136658 -
2e
Schwender CF, andSunday BR. inventors; US 4012387. ; Chem. Abstr. 1977, 87, 23324 -
2f
Schwender CF, andSunday BR. inventors; DE 2645110. ; Chem. Abstr. 1977, 87, 23327 -
2g
Schromm K,Mentrüp A,Renth E.-O, andFügner A. inventors; DE 2557425. ; Chem. Abstr. 1977, 87, 117898 -
3a
Mikhalev AI.Kon’shin ME.Ovodenko LA.Zaks AS. Pharm. Chem. J. (Engl. Transl.) 1995, 29: 124 -
3b
Mikhalev AI.Konshin ME.Yanborisova OA.Zaks AS.Yushkov VV. Pharm. Chem. J. (Engl. Transl.) 1991, 25: 710 -
4a
Palmer BD.Rewcastle GW.Atwell GJ.Baguley BC.Denny WA. J. Med. Chem. 1988, 31: 707 -
4b
Dodic N.Dumaitre B.Daugan A.Pianetti P. J. Med. Chem. 1995, 38: 2418 -
5a
Pellón RF.Martin A.Docampo ML.Mesa M. Synth. Commun. 2006, 36: 1715 -
5b
Docampo Palacios ML.Pellón Comdom RF. Synth. Commun. 2003, 33: 1777 -
5c
Pellón RF.Carrasco R.Rodes L. Synth. Commun. 1996, 26: 3869 -
5d
Koekoesi J.Hermecz I.Szasz G.Meszaros Z. Tetrahedron Lett. 1981, 22: 4861 -
5e
Deetz MJ.Malerich JP.Beatty AM.Smith BD. Tetrahedron Lett. 2001, 42: 1851 -
6a
Paterson T.Smalley RK.Suschitzky H.Barker AJ. J. Chem. Soc., Perkin Trans. 1 1980, 633 -
6b
Mogilaiah K.Rani JU.Sakram B. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 2006, 45: 1584 -
6c
Mogilaiah K.Kankaiah G. Indian J. Chem., Sect. B 2003, 42: 192 -
6d
Mulwad VV.Dalvi MB. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2003, 42: 358 -
6e
Mulwad VV.Lohar MV. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2003, 42: 2567 -
7a
Volovenko YuM.Blyumin EV.Volovnenko TA.Shokol TV.Shishkin OV. Synthesis 2004, 2659 -
7b
Khilya OV.Volovnenko TA.Turov AV.Volovenko YuM. Chem. Heterocycl. Compd. (Engl. Transl.) 2004, 40: 1063 -
7c
Khilya OV.Volovnenko TA.Turov AV.Volovenko YuM. Ukr. Khim. Zh. 2003, 69: 55 ; Chem. Abstr. 2003, 140, 217587 - 8
Tilley JW.Coffen DL.Schaer BH.Lind JJ. J. Org. Chem. 1987, 52: 2469 -
9a
Tinney FJ.Cetenko W.Kerbleski JJ.Connor DT.Sorenson RJ.Herzig DJ. J. Med. Chem. 1981, 24: 878 -
9b
Connor DT.Sorenson RJ.Cetenko WA.Kerbleski JJ.Tinney FJ. J. Med. Chem. 1984, 27: 528 -
10a
Manhas MS.Amin SG. J. Heterocycl. Chem. 1976, 13: 903 -
10b
Csukonyi K.Lazar J.Bernath G.Hermecz I.Meszaros Z. Monatsh. Chem. 1986, 117: 1295 -
10c
Queiroz M.-JRP.Begouin A.Ferreire ICFR.Kirsch G.Calhelha RC.Barbosa S.Estevinho LM. Eur. J. Org. Chem. 2004, 3679 - For reviews, see:
-
11a
Ghosh CK. J. Heterocycl. Chem. 1983, 20: 1437 -
11b
Sabitha G. Aldrichimica Acta 1996, 29: 15 -
11c
Ghosh CK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1997, 36: 968 -
11d
Ghosh CK. Heterocycles 2004, 63: 2875 -
12a
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Tolmachev AA. Synlett 2004, 2287 -
12b
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Tolmachev AA. Synthesis 2007, 1861 -
12c
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Tolmachev AA. Synthesis 2007, 3155 -
13a
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Tolmachev AA. Synthesis 2006, 3715 -
13b
Ryabukhin SV.Plaskon AS.Ostapchuk EN.Volochnyuk DM.Tolmachev AA. Synthesis 2007, 417 -
13c
Ryabukhin SV.Volochnyuk DM.Plaskon AS.Naumchik VS.Tolmachev AA. Synthesis 2007, 1214 -
13d
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Shivanyuk AN.Tolmachev AA. Synthesis 2007, 2872 -
13e
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Shivanyuk AN.Tolmachev AA. J. Org. Chem. 2007, 72: 7417 -
13f
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Pipko SE.Shivanyuk AN.Tolmachev AA. J. Comb. Chem. 2007, 9: 1073