Download PDF
Joule, J. A. et al.: 2017 Science of Synthesis, 2017/1: Knowledge Updates 2017/1 DOI: 10.1055/sos-SD-110-01022
Knowledge Updates 2017/1

10.22.4 Product Subclass 4: 1,2-Dihydroazaindol-3-ones

More Information

Book

Editors: Joule, J. A.; Krause, N.; Oestreich, M.; Rademann, J.; Schaumann, E.; Wirth, T.

Authors: Albericio, F.; Atodiresei, I.; Baba, A.; Baker, A.; Braun, M.; Cherkupally, P.; Delvos, L.; Govender, T.; Hardman-Baldwin, A. M.; Joseph, B.; Kleeberg, C.; Kruger, H. G.; Mattson, A. E.; Mérour, J.-Y.; Nishimoto, Y.; Oestreich, M.; Qian, D.; Ramesh, S.; Rueping, M.; Singh, F. V.; de la Torre, B. G.; Wirth, T.; Yasuda, M.; Zhang, J.

Title: Knowledge Updates 2017/1

Print ISBN: 9783132414105; Online ISBN: 9783132414136; Book DOI: 10.1055/b-004-140261

1st edition © 2017 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

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 reviews the synthesis and reactivity of 1,2-dihydroazaindol-3-ones (azaindoxyls) and related 1,2-dihydroazaindol-3-yl acetates. Synthetic preparations are reviewed for all isomers except for 1,2-dihydro-3H-pyrrolo[2,3-c]pyridin-3-ones.

Key words

1,2-dihydroazaindol-3-ones - azaindoxyls - 1,2-dihydroazaindol-3-yl acetates - cyclization - C2-aldolization
 
  • 1 Luettke W, Hunsdiecker D. Chem. Ber. 1966; 99: 2146
  • 2 Posner T, Kemper W. Ber. Dtsch. Chem. Ges. B 1924; 57: 1311
  • 3 Reindel F. Ber. Dtsch. Chem. Ges. B 1924; 57: 1381
  • 4 Kägi H. Helv. Chim. Acta 1941; 24: 141E
  • 5 Gaywood AP, McNab H. Org. Biomol. Chem. 2010; 8: 5166
    PubMed
  • 6 Anderson RJ, Hill JB, Morris JC. J. Org. Chem. 2005; 70: 6204
    PubMed
  • 7 Mérour J.-Y, Gadonneix P, Malapel-Andrieu B, Desarbre E. Tetrahedron 2001; 57: 1995
  • 8 Desarbre E, Mérour J.-Y. Tetrahedron Lett. 1994; 35: 1995
  • 9 Dropinski JF, Akiyama T, Einstein M, Habulihaz B, Doebber T, Berger JP, Meinke PT, Shi GQ. Bioorg. Med. Chem. Lett. 2005; 15: 5035
  • 10 Goodacre SC, Williams K, Price S, Dyke HJ, Montana JG, Stanley MS, Bao L, Lee W. WO 2008 067 481, 2008 Chem. Abstr. 2008 149 32286
    PubMed
  • 11 Desarbre E, Mérour J.-Y. Tetrahedron Lett. 1996; 37: 43
  • 12 Robba M, Laduree D. Heterocycles 1984; 22: 303
  • 13 Aiello F, Garofalo A, Grande F. Tetrahedron Lett. 2010; 51: 6635
  • 14 Aiello F, Garofalo A, Grande F. Tetrahedron Lett. 2011; 52: 5824
  • 15 Sucharda E. Rocz. Chem. 1923; 3: 236 Chem. Abstr. 1925; 19: 407
  • 16 Tschitschibabin AE. Ber. Dtsch. Chem. Ges. B 1924; 57: 2092
  • 17 Sucharda E. Ber. Dtsch. Chem. Ges. B 1925; 58: 1724
  • 18 Koenigs E, Kantrowitz H. Ber. Dtsch. Chem. Ges. B 1927; 60: 2097
  • 19 Holt SJ, Sadler PW. Proc. R. Soc. London, Ser. B 1958; 148: 481
  • 20 Willette RE. J. Chem. Soc. 1965; 5874
  • 21 Tverdokhlebov V, Denisenko AV, Tolmachev AA, Volovenko YM. Synthesis 2007; 1811
  • 22 Parrick CK, Wilcox R, Kelly AH. J. Chem. Soc., Perkin Trans. 1 1980; 132
  • 23 Cheng X, Merz K.-H, Vatter S, Christ J, Wolfl S, Eisenbrand G. Bioorg. Med. Chem. 2014; 22: 247
    PubMed
  • 24 Desarbre E Ph.D. Dissertation, Université d’Orléans 1995
    PubMed