Polymer-supported synthesis of N-substituted anthranilates as the building blocks for preparation of N-arylated 3-hydroxyquinolin-4(1H)-ones

. 2021 Mar 01 ; 11 (16) : 9362-9365. [epub] 20210302

Status PubMed-not-MEDLINE Jazyk angličtina Země Velká Británie, Anglie Médium electronic-ecollection

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/pmid35423420

Fast and simple access to N-arylated 3-hydroxyquinolin-4(1H)-ones starting from easily available 1-methyl-2-iodoterephthalate and variously substituted anilines is presented. N-Alkylated anthranilic acid derivatives represent important intermediates. They can be advantageously prepared by solid-phase synthesis, by Buchwald-Hartwig amination or reductive amination with wide substrate scope and with excellent crude purities.

Zobrazit více v PubMed

Rehulka J. Vychodilová K. Krejci P. Gurska S. Hradil P. Hajduch M. Dzubak P. Hlavac J. Eur. J. Med. Chem. 2020;192:112176. doi: 10.1016/j.ejmech.2020.112176. PubMed DOI

Burglova K. Rylova G. Markos A. Prichystalova H. Soural M. Petracek M. Medvedikova M. Tejral G. Sopko B. Hradil P. Dzubak P. Hajduch M. Hlavac J. J. Med. Chem. 2018;61:3027–3036. doi: 10.1021/acs.jmedchem.8b00078. PubMed DOI

Hradil P. Hlavac J. Soural M. Hajduch M. Kolar M. Vecerova R. Mini-Rev. Med. Chem. 2009;9:696–702. doi: 10.2174/138955709788452720. PubMed DOI

Hradil P. Jirman J. Collect. Czech. Chem. Commun. 1995;60:1357–1366. doi: 10.1135/cccc19951357. DOI

Soural M. Krchnak V. J. Comb. Chem. 2007;9:793–796. doi: 10.1021/cc070071v. PubMed DOI PMC

Soural M. Hlavac J. Funk P. Dzubak P. Hajduch M. ACS Comb. Sci. 2011;13:39–44. doi: 10.1021/co100013t. PubMed DOI

Soural M. Hlavac J. Hradil P. Frysova I. Hajduch M. Bertolasi V. Malon M. Eur. J. Med. Chem. 2006;41:467–474. doi: 10.1016/j.ejmech.2005.12.008. PubMed DOI

Hradil P. Hlavac J. Lemr K. J. Heterocycl. Chem. 1999;36:141–144. doi: 10.1002/jhet.5570360121. DOI

Spacilova L. Hlavac J. Hradil P. Frysova I. Soural M. Krejci P. Malon M. J. Heterocycl. Chem. 2006;43:1065–1070. doi: 10.1002/jhet.5570430437. DOI

Wang W. Cencic R. Whitesell L. Pelletier J. Porco J. Chem.–Eur. J. 2016;22:12006–12010. doi: 10.1002/chem.201602953. PubMed DOI PMC

Funk P. Motyka K. Dzubak P. Znojek P. Gurska S. Kusz J. McMaster C. Hajduch M. Soural M. RSC Adv. 2015;5:48861–48867. doi: 10.1039/C5RA08733C. DOI

Motyka K. Hlavac J. Soural M. Hradil P. Krejci P. Kvapil L. Weiss M. Tetrahedron Lett. 2011;52:715–717. doi: 10.1016/j.tetlet.2010.12.013. DOI

Sharma S. Srivastava V. K. Kumar A. Eur. J. Med. Chem. 2002;37:689–697. doi: 10.1016/S0223-5234(02)01340-5. PubMed DOI

Varnavas A. Lassiani L. Valenta V. Berti F. Mennuni L. Makovec F. Bioorg. Med. Chem. 2003;11:741–751. doi: 10.1016/S0968-0896(02)00475-3. PubMed DOI

Sun J. F. Xu Y. J. Kong X. H. Su Y. Wang Z. Y. Neurosci. Lett. 2019;696:67–73. doi: 10.1016/j.neulet.2018.12.008. PubMed DOI

Rao H. Fu H. Jiang Y. Zhao Y. J. Org. Chem. 2005;70:8107–8109. doi: 10.1021/jo051221w. PubMed DOI

Rao H. Jin Y. Fu H. Jiang Y. Zhao Y. Chem.–Eur. J. 2006;12:3636–3646. doi: 10.1002/chem.200501473. PubMed DOI

Liu S. Xu L. Asian J. Org. Chem. 2018;7:1856–1863. doi: 10.1002/ajoc.201800371. DOI

Ando S. Hirota Y. Matsunaga H. Ishizuka T. Tetrahedron Lett. 2019;60:1277–1280. doi: 10.1016/j.tetlet.2019.04.004. DOI

Guram A. S. Rennels R. A. Buchwald S. L. Angew. Chem., Int. Ed. Engl. 1995;34:1348–1350. doi: 10.1002/anie.199513481. DOI

Louie J. Hartwig J. F. Tetrahedron Lett. 1995;36:3609–3612. doi: 10.1016/0040-4039(95)00605-C. DOI

Zimmermann V. Brase S. J. Comb. Chem. 2007;9:1114–1137. doi: 10.1021/cc700105p. PubMed DOI

Brown R. C. D. Keily J. Karim R. Tetrahedron Lett. 2000;41:3247–3251. doi: 10.1016/S0040-4039(00)00359-2. DOI

Krajcovicova S. Stankova J. Dzubak P. Hajduch M. Soural M. Urban M. Chem.–Eur. J. 2018;24:4957–4966. doi: 10.1002/chem.201706093. PubMed DOI

Apodaca R. Xiao W. Org. Lett. 2001;3:1745–1748. doi: 10.1021/ol015948s. PubMed DOI

Volná T. Motyka K. Hlaváč J. Chromatographia. 2016;79:1153–1163. doi: 10.1007/s10337-016-3129-6. DOI

Soural M. Hradil P. Krupkova S. Hlavac J. Mini-Rev. Org. Chem. 2012;9:426–432. doi: 10.2174/157019312804699483. DOI

Oza V. B. Petrassi H. M. Purkey H. E. Kelly J. W. Bioorg. Med. Chem. Lett. 1999;9:1–6. doi: 10.1016/S0960-894X(98)00696-9. PubMed DOI

Tiwari D. Haque S. Misra S. Chandra R. Int. J. Drug Dev. Res. 2011;3:265–271.

Kelly J. X. Smilkstein M. J. Brun R. Wittlin S. Cooper R. A. Lane K. D. Janowsky A. Johnson R. A. Dodean R. A. Winter R. Hinrichs D. J. Riscoe M. K. Nature. 2009;459:270–273. doi: 10.1038/nature07937. PubMed DOI PMC

Goodell J. R. Madhok A. A. Hiasa H. Ferguson D. M. Bioorg. Med. Chem. 2006;14:5467–5480. doi: 10.1016/j.bmc.2006.04.044. PubMed DOI

Goodell J. R. Puig-Basagoiti F. Forshey B. M. Shi P. Y. Ferguson D. M. J. Med. Chem. 2006;49:2127–2137. doi: 10.1021/jm051229y. PubMed DOI

Benoit A. R. Schiaffo C. Salomon C. E. Goodell J. R. Hiasa H. Ferguson D. M. Bioorg. Med. Chem. Lett. 2014;24:3014–3017. doi: 10.1016/j.bmcl.2014.05.037. PubMed DOI

Watterson S. H. Chen P. Zhao Y. Gu H. H. Dhar T. G. M. Xiao Z. Ballentine S. K. Shen Z. Fleener C. A. Rouleau K. A. Obermeier M. Yang Z. McIntyre K. W. Shuster D. J. Witmer M. Dambach D. Chao S. Mathur A. Chen B. C. Barrish J. C. Robl J. A. Townsend R. Iwanowicz E. J. J. Med. Chem. 2007;50:3730–3742. doi: 10.1021/jm070299x. PubMed DOI

Howell L. A. Howman A. O'Connell M. A. Mueller A. Searcey M. Bioorg. Med. Chem. Lett. 2009;19:5880–5883. doi: 10.1016/j.bmcl.2009.08.070. PubMed DOI

James L. I. Korboukh V. K. Krichevsky L. Baughman B. M. Herold J. M. Norris J. L. Jin J. Kireev D. B. Janzen W. P. Arrowsmith C. H. Frye S. V. J. Med. Chem. 2013;56:7358–7371. doi: 10.1021/jm400919p. PubMed DOI PMC

Najít záznam

Citační ukazatele

Nahrávání dat ...

Možnosti archivace

Nahrávání dat ...