Literature DB >> 20438102

Nucleophilic substitution of oxazino-/oxazolino-/benzoxazin [3,2-b]indazoles: an effective route to 1H-indazolones.

Michael B Donald1, Wayne E Conrad, James S Oakdale, Jeffrey D Butler, Makhluf J Haddadin, Mark J Kurth.   

Abstract

A variety of nucleophiles, thiolates, alkoxides, amines, iodide, and cyanide, react with oxazino-, oxazolino-, and benzoxazin[3,2-b]indazoles under microwave conditions to yield a diverse set of 2-substituted 1H-indazolones. The synthetic utility of these indazoles is further demonstrated by ANRORC (addition of the nucleophile, ring-opening, and ring closure) reactions to yield isomeric pyrazoloindazolones by a process wherein iodide acts first as a nucleophile and subsequently as a leaving group.

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Year:  2010        PMID： 20438102      PMCID： PMC3108055          DOI： 10.1021/ol100751n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Structure-based drug design of a highly potent CDK1,2,4,6 inhibitor with novel macrocyclic quinoxalin-2-one structure.

Authors:  Nobuhiko Kawanishi; Tetsuya Sugimoto; Jun Shibata; Kaori Nakamura; Kouta Masutani; Mari Ikuta; Hiroshi Hirai
Journal:  Bioorg Med Chem Lett       Date:  2006-07-28       Impact factor: 2.823

2.  A general and mild palladium-catalyzed domino reaction for the synthesis of 2H-indazoles.

Authors:  Nis Halland; Marc Nazaré; Omar R'kyek; Jorge Alonso; Matthias Urmann; Andreas Lindenschmidt
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Chemical modification of the insecticidal briantheins X and Y.

Authors:  John M Cronan; Angela Lee; Jun Liang; Jon Clardy; John H Cardellina
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050

4.  Identification of an agent selectively targeting DPC4 (deleted in pancreatic cancer locus 4)-deficient pancreatic cancer cells.

Authors:  Hong Wang; Haiyong Han; Daniel D Von Hoff
Journal:  Cancer Res       Date:  2006-10-01       Impact factor: 12.701

Review 5.  Pharmacological properties of indazole derivatives: recent developments.

Authors:  Hugo Cerecetto; Alejandra Gerpe; Mercedes González; Vicente J Arán; Carmen Ochoa de Ocáriz
Journal:  Mini Rev Med Chem       Date:  2005-10       Impact factor: 3.862

6.  Regioselective synthesis of 1-alkyl- or 1-aryl-1H-indazoles via copper-catalyzed cyclizations of 2-haloarylcarbonylic compounds.

Authors:  Dolores Viña; Esther del Olmo; José L López-Pérez; Arturo San Feliciano
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

7.  The search for novel TRPV1-antagonists: from carboxamides to benzimidazoles and indazolones.

Authors:  Stephen Robert Fletcher; Edward McIver; Stephen Lewis; Frank Burkamp; Clare Leech; Glenn Mason; Susan Boyce; Denise Morrison; Gillian Richards; Kathy Sutton; Anthony Brian Jones
Journal:  Bioorg Med Chem Lett       Date:  2006-03-24       Impact factor: 2.823

8.  Efficient and convenient synthesis of indazol-3(2H)-ones and 2-aminobenzonitriles.

Authors:  Guolan Dou; Daqing Shi
Journal:  J Comb Chem       Date:  2009 Nov-Dec

9.  An oxazolo[3,2-b]indazole route to 1H-indazolones.

Authors:  James S Oakdale; Danielle M Solano; James C Fettinger; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

10.  Synthesis and antiinflammatory activity of novel indazolones.

Authors:  Khaled A M Abouzid; H S el-Abhar
Journal:  Arch Pharm Res       Date:  2003-01       Impact factor: 4.946
  10 in total
  8 in total

1.  Inhibition of myeloperoxidase: evaluation of 2H-indazoles and 1H-indazolones.

Authors:  Aaron Roth; Sean Ott; Kelli M Farber; Teresa A Palazzo; Wayne E Conrad; Makhluf J Haddadin; Dean J Tantillo; Carroll E Cross; Jason P Eiserich; Mark J Kurth
Journal:  Bioorg Med Chem       Date:  2014-10-02       Impact factor: 3.641

2.  Davis-Beirut Reaction: Diverse Chemistries of Highly Reactive Nitroso Intermediates in Heterocycle Synthesis.

Authors:  Jie S Zhu; Makhluf J Haddadin; Mark J Kurth
Journal:  Acc Chem Res       Date:  2019-07-22       Impact factor: 22.384

3.  The Davis-Beirut reaction: N1,N2-disubstituted-1H-indazolones via 1,6-electrophilic addition to 3-alkoxy-2H-indazoles.

Authors:  Wayne E Conrad; Ryo Fukazawa; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2011-05-25       Impact factor: 6.005

4.  A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles.

Authors:  Wayne E Conrad; Kevin X Rodriguez; Huy H Nguyen; James C Fettinger; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2012-07-23       Impact factor: 6.005

5.  Davis-Beirut Reaction: A Photochemical Brønsted Acid Catalyzed Route to N-Aryl 2H-Indazoles.

Authors:  Niklas Kraemer; Clarabella J Li; Jie S Zhu; Julio M Larach; Ka Yi Tsui; Dean J Tantillo; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2019-07-24       Impact factor: 6.005

6.  Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1H-indoles, and quinolin-4(1H)-ones.

Authors:  Keith C Coffman; Teresa A Palazzo; Timothy P Hartley; James C Fettinger; Dean J Tantillo; Mark J Kurth
Journal:  Org Lett       Date:  2013-04-04       Impact factor: 6.005

7.  Acid and base catalyzed Davis-Beirut reaction: experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles.

Authors:  Belem Avila; Mohammad H El-Dakdouki; Musa Z Nazer; Jason G Harrison; Dean J Tantillo; Makhluf J Haddadin; Mark J Kurth
Journal:  Tetrahedron Lett       Date:  2012-09-15       Impact factor: 2.415

8.  Davis-Beirut reaction: route to thiazolo-, thiazino-, and thiazepino-2H-indazoles.

Authors:  Kelli M Farber; Makhluf J Haddadin; Mark J Kurth
Journal:  J Org Chem       Date:  2014-07-23       Impact factor: 4.354
  8 in total

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