Download PDF
Aitken, R. A. et al.: 2016 Science of Synthesis, 2015/2: Knowledge Updates 2015/2 DOI: 10.1055/sos-SD-116-00978
Knowledge Updates 2015/2

16.10.5 Phthalazines (Update 2015)

More Information

Book

Editors: Aitken, R. A.; Brønsted Nielsen, M.; Drabowicz, J.; Li, J. J.; Plietker, B.; Wirth, T.

Authors: Banert, K.; Brønsted Nielsen, M.; Cacciarini, M.; Elliott, M.; Grün, A.; Hagen, T.; Helgren, T.; Hennecke, U.; Iskra, J.; Kang, F.-A.; Keglevich, G.; Larsen, M. H.; Li, H.; Mazet, C.; Murphree, S.S.; Nomoto, A.; Ogawa, A.; Reißig, H.-U.; Saleh, B. A.; Singh, F. V. ; Tomé, A. C.; Wirth, T.; Yang, S.-M.; Zimmer, R.

Title: Knowledge Updates 2015/2

Print ISBN: 9783131984616; Online ISBN: 9783131975812; Book DOI: 10.1055/b-003-125870

1st Edition © 2016 Georg Thieme Verlag KG
Georg Thieme Verlag, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

Also available at
 

Abstract

This chapter is an update to the earlier Science of Synthesis contribution (Section 16.10) concerning the synthesis and reactions of phthalazines. Literature from 2004 to early 2014 has been considered. The major focus since the initial publication involves phthalazine substituent modification rather than the synthesis of phthalazine rings.

Key words

phthalazines - 2,3-dihydrophthalazine-1,4-diones - multicomponent reactions - cyclization - heteroarylation - cross coupling - hypervalent iodine
 
  • 1 Vlaar T., Ruijter E., Znabet A., Janssen E., de Kanter F. J. J., Maes B. U. W., Orru R. V. A. Org. Lett. 2011; 13: 6496
  • 2 Vlaar T., Mampuys P., Helliwell M., Maes B. U. W., Orru R. V. A., Ruijter E. J. Org. Chem. 2013; 78: 6735
  • 3 Kessler S. N., Wegner H. A. Org. Lett. 2012; 14: 3268
  • 4 Bel Abed H., Bande O., Mammoliti O., Van Lommen G., Herdewijn P. Tetrahedron Lett. 2013; 54: 7056
  • 5 Vasilevsky S. F., Mikhailovskaya T. F., Mamatyuk V. I., Salnikov G. E., Bogdanchikov G. A., Manoharan M., Alabugin I. V. J. Org. Chem. 2009; 74: 8106
  • 6 Vasilevsky S. F., Mikhailovskaya T. F. Chem. Heterocycl. Compd. (Engl. Transl.) 2009; 45: 55
  • 7 Özer G., Saracoglu N., Menzek A., Balci M. Tetrahedron 2005; 61: 1545
  • 8 Özer G., Saracoglu N., Balci M. J. Org. Chem. 2003; 68: 7009
  • 9 Venkatraj M., Ariën K. K., Heeres J., Dirié B., Joossens J., Van Goethem S., Van Der Veken P., Michiels J., Vande Velde C. M. L., Vanham G., Lewi P. J., Augustyns K. Bioorg. Med. Chem. 2011; 19: 5924
  • 10 Brown B. S., Li T., Peddi S., Perez-Medrano A., DeGoey D.. US 2012 0289 500, 2012
  • 11 Matcha K., Antonchick A. P. Angew. Chem. 2013; 125: 2136 Angew. Chem. Int. Ed. 2013; 52: 2082
  • 12 Antonchick A. P., Burgmann L. Angew. Chem. 2013; 125: 3349 Angew. Chem. Int. Ed. 2013; 52: 3267
  • 13 Seiple I. B., Su S., Rodriguez R. A., Gianatassio R., Fujiwara Y., Sobel A. L., Baran P. S. J. Am. Chem. Soc. 2010; 132: 13 194
  • 14 Duncton M. A. J., Estiarte M. A., Johnson R. J., Cox M., O’Mahoney D. J. R., Edwards W. T., Kelly M. G. J. Org. Chem. 2009; 74: 6354
  • 15 Schipper D. J., El-Salfiti M., Whipp C. J., Fagnou K. Tetrahedron 2009; 65: 4977
  • 16 Yamaguchi A. D., Mandal D., Yamaguchi J., Itami K. Chem. Lett. 2011; 40: 555
  • 17 Ryu C.-K., Park R.-E., Ma M.-Y., Nho J.-H. Bioorg. Med. Chem. Lett. 2007; 17: 2577
  • 18 Paige M., Kosturko G., Bulut G., Miessau M., Rahim S., Toretsky J. A., Brown M. L., Üren A. Bioorg. Med. Chem. 2014; 22: 478
  • 19 Kim J. S., Rhee H.-K., Park H. J., Lee S. K., Lee C.-O., Park Choo H.-Y. Bioorg. Med. Chem. 2008; 16: 4545
  • 20 Rastogi S. K., Medellin D. C., Kornienko A. Org. Biomol. Chem. 2014; 12: 410
  • 21 El-Hashash M. A., El-Badry Y. A. J. Chem. Pharm. Res. 2012; 4: 2354
  • 22 Hellal M., Bihel F., Mongeot A., Bourguignon J.-J. Org. Biomol. Chem. 2006; 4: 3142
  • 23 Pal M., Batchu V. R., Parasuraman K., Yeleswarapu K. R. J. Org. Chem. 2003; 68: 6806
  • 24 Abd El-Wahab A. H. F., Mohamed H. M., El-Agrody A. M., El-Nassag M. A., Bedair A. H. Eur. J. Chem. 2013; 4: 10
  • 25 Subasinghe N. L., Lanter J., Markotan T., Opas E., McKenney S., Crysler C., Hou C., O’Neill J., Johnson D., Sui Z. Bioorg. Med. Chem. Lett. 2013; 23: 1063
  • 26 Elagawany M., Ibrahim M. A., Ali Ahmed H. E., El-Etrawy A. Sh., Ghiaty A., Abdel-Samii Z. K., El-Feky S. A., Bajorath J. Bioorg. Med. Chem. Lett. 2013; 23: 2007
  • 27 Herberich B., Cao G.-Q., Chakrabarti P. P., Falsey J. R., Pettus L., Rzasa R. M., Reed A. B., Reichelt A., Sham K., Thaman M., Wurz R. P., Xu S., Zhang D., Hsieh F., Lee M. R., Syed R., Li V., Grosfeld D., Plant M. H., Henkle B., Sherman L., Middleton S., Wong L. M., Tasker A. S. J. Med. Chem. 2008; 51: 6271
  • 28 Lee H.-J., Kim J. S., Park S.-Y., Suh M.-E., Kim H. J., Seo E.-K., Lee C.-O. Bioorg. Med. Chem. 2004; 12: 1623
  • 29 Haider N., Kabicher T., Käferböck J., Plenk A. Molecules 2007; 12: 1900
  • 30 Haider N., Käferböck J. Tetrahedron 2004; 60: 6495
  • 31 Deng Z., Tseng H.-W., Zong R., Wang D., Thummel R. Inorg. Chem. 2008; 47: 1835
  • 32 Pettus L. H., Xu S., Cao G.-Q., Chakrabarti P. P., Rzasa R. M., Sham K., Wurz R. P., Zhang D., Middleton S., Henkle B., Plant M. H., Saris C. J. M., Sherman L., Wong L. M., Powers D. A., Tudor Y., Yu V., Lee M. R., Syed R., Hsieh F., Tasker A. S. J. Med. Chem. 2008; 51: 6280
  • 33 Duncton M. A. J., Singh R. Org. Lett. 2013; 15: 4284
  • 34 Zbancioc G., Bejan V., Risca M., Moldoveanu C., Mangalagiu I. I. Molecules 2009; 14: 403
  • 35 Prakash O., Aneja D. K., Hussain K., Kumar R., Arora S., Sharma C., Aneja K. R. J. Heterocycl. Chem. 2012; 49: 1091
  • 36 Hemdan M. M., Taha S. M., Gabr A. M., Elkady M. Y. J. Chem. Res. 2010; 34: 102
  • 37 Rauws T. R. M., Biancalani C., De Schutter J. W., Maes B. U. W. Tetrahedron 2010; 66: 6958
  • 38 Sun X.-Y., Guan L.-P., Zhang L., Wei C.-X., Piao H.-R., Quan Z.-S. J. Braz. Chem. Soc. 2009; 20: 826
  • 39 De P., Yoya G. K., Constant P., Bedos-Belval F., Duran H., Saffon N., Daffé M., Baltas M. J. Med. Chem. 2011; 54: 1449
  • 40 Parenty A. D. C., Song Y.-F., Richmond C. J., Cronin L. Org. Lett. 2007; 9: 2253
  • 41 Fernández N., Carrillo L., Vicario J. L., Badía D., Reyes E. Chem. Commun. (Cambridge) 2011; 47: 12 313
  • 42 Butler R. N., Coyne A. G., Cunningham W. J., Moloney E. M. J. Org. Chem. 2013; 78: 3276