Synthesis of cis-Isoquinolonic Acids Containing Boronate Esters

Haiwen Zhang; Christopher M. Vogels; Susan L. Wheaton; Felix J. Baerlocher; Andreas Decken; Stephen A. Westcott

doi:10.1055/s-2005-872124

PAPER

Synthesis of cis-Isoquinolonic Acids Containing Boronate Esters

Haiwen Zhang^a, Christopher M. Vogels^a, Susan L. Wheaton^a, Felix J. Baerlocher^b, Andreas Decken^c, Stephen A. Westcott*^a
^a Department of Chemistry, Mount Allison University, Sackville, NB E4L 1G8, Canada
Fax: +1(506)3642313; e-Mail: swestcott@mta.ca;
^b Department of Biology, Mount Allison University, Sackville, NB E4L 1G7, Canada
^c Department of Chemistry, University of New Brunswick, Fredericton, NB E3B 5A3, Canada

Abstract

All articles of this category

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

Full Text

References

<A NAME="RM01905SS-1">1</A> Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

<A NAME="RM01905SS-2">2</A> Ni W. Fang H. Springsteen G. Wang B. J. Org. Chem. 2004, 69: 1999

<A NAME="RM01905SS-3">3</A> Yang W. Gao X. Wang B. Med. Res. Rev. 2003, 23: 346

<A NAME="RM01905SS-4">4</A> Kumar SK. Hager E. Pettit C. Gurulingappa H. Davidson NE. Khan SR. J. Med. Chem. 2003, 46: 2813

<A NAME="RM01905SS-5">5</A> Cama E. Colleluori DM. Emig FA. Shin H. Kim SW. Kim NN. Traish AM. Ash DE. Christianson DW. Biochemistry 2003, 42: 8445

<A NAME="RM01905SS-6">6</A> Stolowitz ML. Ahlem C. Hughes KA. Kaiser RJ. Kesicki EA. Li G. Lund KP. Torkelson SM. Wiley JP. Bioconjugate Chem. 2001, 12: 229

<A NAME="RM01905SS-7">7</A> Kabalka GW. Das BC. Das S. Tetrahedron Lett. 2001, 42: 7145

<A NAME="RM01905SS-8">8</A> Soloway AH. Tjarks W. Barnum BA. Rong F.-G. Barth RF. Codogni IM. Wilson JG. Chem. Rev. 1998, 98: 1515

<A NAME="RM01905SS-9">9</A> Weston GS. Blazquez J. Baquero F. Shoichet BK. J. Med. Chem. 1998, 41: 4577

<A NAME="RM01905SS-10A">10a</A> Vogels CM. Nikolcheva LG. Spinney HA. Norman DW. Baerlocher MO. Baerlocher FJ. Westcott SA. Can. J. Chem. 2001, 79: 1115

<A NAME="RM01905SS-10B">10b</A> 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

<A NAME="RM01905SS-11">11</A> Gronowitz S. Dalgren T. Namtvedt J. Roos C. Sjöberg B. Forsgren U. Acta Pharm. Suec. 1971, 8: 377

<A NAME="RM01905SS-12">12</A> Chern M.-S. Li W.-R. Tetrahedron Lett. 2004, 45: 8323

<A NAME="RM01905SS-13">13</A> Povarov LS. Russ. Chem. Rev. 1967, 36: 656

<A NAME="RM01905SS-14">14</A> Yamada N. Kadowaki S. Takahashi K. Umezu K. Biochem. Pharmacol. 1992, 44: 1211

<A NAME="RM01905SS-15">15</A> Johnson JV. Rauckman S. Baccanari PD. Roth B. J. Med. Chem. 1989, 32: 1942

<A NAME="RM01905SS-16">16</A> Yadav JS. Reddy BVS. Saritha Raj K. Prasad AR. Tetrahedron 2003, 59: 1805

<A NAME="RM01905SS-17">17</A> Cushman M. Chen LG. J. Org. Chem. 1978, 43: 286

<A NAME="RM01905SS-18">18</A> Govindachari TR. Cinnasamy P. Rajeswari S. Chandrasekaran S. Pramila MS. Natarajan S. Nagarajan K. Pai BR. Heterocycles 1984, 22: 585

<A NAME="RM01905SS-19">19</A> Bogdanov MG. Palamareva MD. Tetrahedron 2004, 60: 2525

<A NAME="RM01905SS-20">20</A> Martichonok V. Jones JB. J. Am. Chem. Soc. 1996, 118: 950

<A NAME="RM01905SS-21">21</A> Moore ANJ. Wayner DDM. Can. J. Chem. 1999, 77: 681

<A NAME="RM01905SS-22">22</A> Hartley JH. Phillips MD. James TD. New J. Chem. 2002, 26: 1228

<A NAME="RM01905SS-23">23</A> Sailes HE. Watts JP. Whiting A. Tetrahedron Lett. 2000, 41: 2457

<A NAME="RM01905SS-24">24</A> Kaneti J. Bakalova SM. Pojarlieff IG. J. Org. Chem. 2003, 68: 6824

<A NAME="RM01905SS-25">25</A> Cushman M. Gentry J. Dekow FW. J. Org. Chem. 1977, 42: 1111

<A NAME="RM01905SS-26">26</A> Nöth H. Wrackmeyer B. In Nuclear Magnetic Resonance Spectroscopy of Boron Compounds Springer-Verlag; Berlin: 1987.

<A NAME="RM01905SS-27">27</A> Höpfl H. Sánchez M. Barba V. Farfán N. Rojas S. Santillan R. Inorg. Chem. 1998, 37: 1679

<A NAME="RM01905SS-28">28</A> Georgieva A. Stanoeva E. Karamfilova K. Spassov S. Angelova O. Haimova M. De Kimpe N. Boelens M. Tetrahedron 1994, 50: 9399

<A NAME="RM01905SS-29">29</A> 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

<A NAME="RM01905SS-30">30</A> 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

<A NAME="RM01905SS-31">31</A> Nguyen P. Coapes RB. Woodward AD. Taylor NJ. Burke JM. Howard JAK. Marder TB. J. Organomet. Chem. 2002, 652: 77

<A NAME="RM01905SS-32">32</A> 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

<A NAME="RM01905SS-33">33</A> Bringmann G. Günther C. Peters E.-M. Peters K. Tetrahedron 2001, 57: 1253

<A NAME="RM01905SS-34">34</A> Gößnitzer E. Punkenhofer A. Amon A. Favre B. Eur. J. Pharm. Sci. 2003, 19: 151

<A NAME="RM01905SS-35">35</A> Barrett AGM. Seefeld MA. White AJP. Williams DJ. J. Org. Chem. 1996, 61: 2677

<A NAME="RM01905SS-36">36</A> Baerlocher FJ. Baerlocher MO. Chaulk CL. Langler RF. MacQuarrie SL. Aust. J. Chem. 2000, 53: 399

<A NAME="RM01905SS-37">37</A> SAINT 6.02 Bruker AXS, Inc.; Madison, Wisconsin, USA: 1997-1999.

<A NAME="RM01905SS-38">38</A> Sheldrick GM. SADABS Bruker AXS, Inc.; Madison, Wisconsin, USA: 1999.

<A NAME="RM01905SS-39">39</A> Sheldrick GM. SHELXTL 5.1 Bruker AXS, Inc.; Madison, Wisconsin, USA: 1997.