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Synthesis 2005(16): 2739-2743
DOI: 10.1055/s-2005-872124
DOI: 10.1055/s-2005-872124
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of cis-Isoquinolonic Acids Containing Boronate Esters
Further Information
Received
10 April 2005
Publication Date:
04 August 2005 (online)
Publication History
Publication Date:
04 August 2005 (online)
Abstract
The addition of homophthalic anhydride to aldimines derived from pinacolation of 4-formylphenylboronic acid selectively gives the corresponding cis-isoquinolonic acids. Reactions proceed without the need for an additional Lewis acid catalyst at room temperature.
Key words
aldimines - antifungal - boronate esters - cyclocondensation - isoquinolines
- 1
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 - 2
Ni W.Fang H.Springsteen G.Wang B. J. Org. Chem. 2004, 69: 1999 - 3
Yang W.Gao X.Wang B. Med. Res. Rev. 2003, 23: 346 - 4
Kumar SK.Hager E.Pettit C.Gurulingappa H.Davidson NE.Khan SR. J. Med. Chem. 2003, 46: 2813 - 5
Cama E.Colleluori DM.Emig FA.Shin H.Kim SW.Kim NN.Traish AM.Ash DE.Christianson DW. Biochemistry 2003, 42: 8445 - 6
Stolowitz ML.Ahlem C.Hughes KA.Kaiser RJ.Kesicki EA.Li G.Lund KP.Torkelson SM.Wiley JP. Bioconjugate Chem. 2001, 12: 229 - 7
Kabalka GW.Das BC.Das S. Tetrahedron Lett. 2001, 42: 7145 - 8
Soloway AH.Tjarks W.Barnum BA.Rong F.-G.Barth RF.Codogni IM.Wilson JG. Chem. Rev. 1998, 98: 1515 - 9
Weston GS.Blazquez J.Baquero F.Shoichet BK. J. Med. Chem. 1998, 41: 4577 -
10a
Vogels CM.Nikolcheva LG.Spinney HA.Norman DW.Baerlocher MO.Baerlocher FJ.Westcott SA. Can. J. Chem. 2001, 79: 1115 -
10b
Irving AM.Vogels CM.Nikolcheva LG.Edwards JP.He X.-F.Hamilton MG.Baerlocher MO.Baerlocher FJ.Decken A.Westcott SA. New J. Chem. 2003, 27: 1419 - 11
Gronowitz S.Dalgren T.Namtvedt J.Roos C.Sjöberg B.Forsgren U. Acta Pharm. Suec. 1971, 8: 377 - 12
Chern M.-S.Li W.-R. Tetrahedron Lett. 2004, 45: 8323 - 13
Povarov LS. Russ. Chem. Rev. 1967, 36: 656 - 14
Yamada N.Kadowaki S.Takahashi K.Umezu K. Biochem. Pharmacol. 1992, 44: 1211 - 15
Johnson JV.Rauckman S.Baccanari PD.Roth B. J. Med. Chem. 1989, 32: 1942 - 16
Yadav JS.Reddy BVS.Saritha Raj K.Prasad AR. Tetrahedron 2003, 59: 1805 - 17
Cushman M.Chen LG. J. Org. Chem. 1978, 43: 286 - 18
Govindachari TR.Cinnasamy P.Rajeswari S.Chandrasekaran S.Pramila MS.Natarajan S.Nagarajan K.Pai BR. Heterocycles 1984, 22: 585 - 19
Bogdanov MG.Palamareva MD. Tetrahedron 2004, 60: 2525 - 20
Martichonok V.Jones JB. J. Am. Chem. Soc. 1996, 118: 950 - 21
Moore ANJ.Wayner DDM. Can. J. Chem. 1999, 77: 681 - 22
Hartley JH.Phillips MD.James TD. New J. Chem. 2002, 26: 1228 - 23
Sailes HE.Watts JP.Whiting A. Tetrahedron Lett. 2000, 41: 2457 - 24
Kaneti J.Bakalova SM.Pojarlieff IG. J. Org. Chem. 2003, 68: 6824 - 25
Cushman M.Gentry J.Dekow FW. J. Org. Chem. 1977, 42: 1111 - 26
Nöth H.Wrackmeyer B. In Nuclear Magnetic Resonance Spectroscopy of Boron Compounds Springer-Verlag; Berlin: 1987. - 27
Höpfl H.Sánchez M.Barba V.Farfán N.Rojas S.Santillan R. Inorg. Chem. 1998, 37: 1679 - 28
Georgieva A.Stanoeva E.Karamfilova K.Spassov S.Angelova O.Haimova M.De Kimpe N.Boelens M. Tetrahedron 1994, 50: 9399 - 29
Coapes RB.Souza FES.Fox MA.Batsanov AS.Goeta AE.Yufit DS.Leech MA.Howard JAK.Scott AJ.Clegg W.Marder TB. J. Chem. Soc., Dalton Trans. 2001, 1201 - 30
Clegg W.Elsegood MRJ.Lawlor FJ.Norman NC.Pickett NL.Robbins EG.Scott AJ.Nguyen P.Taylor NJ.Marder TB. Inorg. Chem. 1998, 37: 5289 - 31
Nguyen P.Coapes RB.Woodward AD.Taylor NJ.Burke JM.Howard JAK.Marder TB. J. Organomet. Chem. 2002, 652: 77 - 32
Iwasa K.Moriyasu M.Tachibana Y.Kim H.-S.Wataya Y.Wiegrebe W.Bastow KF.Costentino LM.Kozuka M.Lee K.-H. Bioorg. Med. Chem. 2001, 9: 2871 - 33
Bringmann G.Günther C.Peters E.-M.Peters K. Tetrahedron 2001, 57: 1253 - 34
Gößnitzer E.Punkenhofer A.Amon A.Favre B. Eur. J. Pharm. Sci. 2003, 19: 151 - 35
Barrett AGM.Seefeld MA.White AJP.Williams DJ. J. Org. Chem. 1996, 61: 2677 - 36
Baerlocher FJ.Baerlocher MO.Chaulk CL.Langler RF.MacQuarrie SL. Aust. J. Chem. 2000, 53: 399 - 37
SAINT 6.02
Bruker AXS, Inc.;
Madison, Wisconsin, USA:
1997-1999.
- 38
Sheldrick GM. SADABS Bruker AXS, Inc.; Madison, Wisconsin, USA: 1999. - 39
Sheldrick GM. SHELXTL 5.1 Bruker AXS, Inc.; Madison, Wisconsin, USA: 1997.