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Synthesis 2009(14): 2333-2340
DOI: 10.1055/s-0029-1216853
DOI: 10.1055/s-0029-1216853
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Novel Procedure for the Synthesis of Benzo[b][1,8]naphthyridine-3-carboxylate Derivatives from Morita-Baylis-Hillman Adduct Acetates
Further Information
Received
2 March 2009
Publication Date:
29 May 2009 (online)
Publication History
Publication Date:
29 May 2009 (online)
Abstract
A novel procedure has been designed for the preparation of benzo[b][1,8]naphthyridine-3-carboxylate derivatives from the reaction of Morita-Baylis-Hillman adduct acetates with primary amines, ammonium acetate or benzenesulfonamides. The approach, which involves readily available starting materials and mild reaction conditions, gives excellent yields after a convenient workup procedure.
Key words
benzo[b][1,8]naphthyridine-3-carboxylate - Morita-Baylis-Hillman adduct acetates - primary amines - ammonium acetate - benzenesulfonamides
-
1a
Ryabukhin SV.Plaskon AS.Volochnyuk DM.Shivanyuk AN.Tolmachev AA. Synthesis 2007, 2872 -
1b
Belmont P.Andrez J.-C.Allan CSM. Tetrahedron Lett. 2004, 45: 2783 -
1c
Smith L.Kiselyov AS. Tetrahedron Lett. 1999, 40: 5643 -
1d
Srivastava RP.Neelima Bhaduri AP. J. Heterocycl. Chem. 1987, 24: 219 -
1e
Mabire D.Coupa S.Adelinet C.Poncelet A.Simonnet Y.Venet M.Wouters R.Lesage ASJ.Beijsterveldt LV.Bischoff F. J. Med. Chem. 2005, 48: 2134 -
2a
Devi I.Baruah B.Bhuyan PJ. Synlett 2006, 2593 -
2b
Wright CW.Addac-Kyereme J.Breen AG.Brown JE.Cox MF.Croft SL.Gokcek Y.Kendrick H.Phillips RM.Pollet PL. J. Med. Chem. 2001, 44: 3187 -
2c
Sahu NP.Pal C.Mandal NB.Banerjee S.Raha M.Kundu AP.Basu A.Ghosh M.Roy K.Bandyopadhyay S. Bioorg. Med. Chem. 2002, 10: 1687 -
2d
Bringmann G.Reichert Y.Kane VV. Tetrahedron 2004, 60: 3539 -
2e
Kournetsov VV.Mendez LYV.Gomez CMM. Curr. Org. Chem. 2005, 9: 141 - 3
Nithyadevi V.Rajendran SP. J. Heterocycl. Chem. 2006, 43: 755 -
4a
Singh V.Batra S. Tetrahedron 2008, 64: 4511 -
4b
Basavaiah D.Rao AJ.Satyanarayana T. Chem. Rev. 2003, 103: 811 -
4c
Shi Y.Shi M. Eur. J. Org. Chem. 2007, 2905 -
4d
Masson G.Housseman C.Zhu J. Angew. Chem. Int. Ed. 2007, 46: 4614 -
4e
Lee KY.Gowrisankar S.Kim JN. Bull. Korean Chem. Soc. 2005, 26: 1481 -
5a
Shi M.Liu XG. Org. Lett. 2008, 10: 1043 -
5b
Basavaiah D.Roy S. Org. Lett. 2008, 10: 1819 -
5c
Zhou A.Hanson PR. Org. Lett. 2008, 10: 2951 -
5d
Krishna PR.Reddy PS. J. Comb. Chem. 2008, 10: 426 -
5e
Mandal SK.Paira M.Roy SC. J. Org. Chem. 2008, 73: 3823 -
5f
Jiang YQ.Shi YL.Shi M. J. Am. Chem. Soc. 2008, 130: 7202 -
5g
Yadav JS.Reddy BVS.Mandal SS.Singh AP.Basak AK. Synthesis 2008, 1943 -
5h
Garre S.Parker E.Ni B.Headley AD. Org. Biomol. Chem. 2008, 6: 3041 -
5i
Abermil N.Masson G.Zhu J. J. Am. Chem. Soc. 2008, 130: 12596 -
6a
Kim JM.Kim KH.Kim TH.Kim JN. Tetrahedron Lett. 2008, 49: 3248 -
6b
Lee HS.Kim SH.Gowrisankar S.Kim JN. Tetrahedron 2008, 64: 7183 -
6c
Lu A.Xu X.Gao P.Zhou Z.Song H.Tang C. Tetrahedron: Asymmetry 2008, 19: 1886 -
6d
Nag S.Mishra A.Batra S. Tetrahedron 2008, 64: 10162 -
6e
Kim JM.Kim SH.Kim SH.Kim JN. Bull. Korean Chem. Soc. 2008, 29: 1583 -
7a
Chen J.Su W.Hua H.Liu M.Jin C. Green Chem. 2007, 9: 972 -
7b
Chen J.Hua H.Jin C.Zhang X.Xie Y.Su W. Green Chem. 2006, 8: 330 -
8a
Zhong W.Zhao Y.Su W. Tetrahedron 2008, 64: 5491 -
8b
Zhong W.Lin F.Chen R.Su W. Synthesis 2008, 2561 -
8c
Zhong W.Zhao Y.Guo B.Wu P.Su W. Synth. Commun. 2008, 38: 3291 -
9a
Ali MM.Tasneem Rajanna KC.Sai-Prakash PK. Synlett 2001, 251 -
9b
Su W.Zhuang Y.Wu D.Zhong W. Org. Prep. Proced. Int. 2007, 39: 195 -
9c
Su W.Li Z.Zhao L. Org. Prep. Proced. Int. 2007, 39: 495 ; Method for the preparation of 2-chloro-3-formyl quinolines 2: the reaction was carried out using bis(trichloromethyl)carbonate BTC/DMF instead of the DMF/POCl3 system. -
10a
Chung YM.Lee HJ.Hwang SS.Kim JN. Bull. Korean Chem. Soc. 2001, 22: 799 -
10b
Chung YM.Kim JN.Im YJ. Tetrahedron Lett. 2002, 43: 6209