Literature DB >> 21660198

Aza-Nazarov cyclization cascades.

Kiran Kumar Solingapuram Sai1, Matthew J O'Connor, Douglas A Klumpp.   

Abstract

Benzamides with tethered acetal groups undergo reactions in CF(3)SO(3)H to give ring-fused isoindolinones by a cyclization cascade. The reaction initially forms an N-acyliminium ion which then gives the isoindolinone by the aza-Nazarov reaction. An unusual variant also cyclizes at the allylic position.

Entities:  

Year:  2011        PMID： 21660198      PMCID： PMC3109674          DOI： 10.1016/j.tetlet.2010.11.164

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  10 in total

1.  Cyclizations of N-acyliminium ions.

Authors:  Bruce E Maryanoff; Han-Cheng Zhang; Judith H Cohen; Ignatius J Turchi; Cynthia A Maryanoff
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

Review 2.  Advances in the Nazarov cyclization.

Authors:  Waka Nakanishi; Frederick G West
Journal:  Curr Opin Drug Discov Devel       Date:  2009-11

3.  Organocatalytic asymmetric aza-Nazarov cyclization of an azirine.

Authors:  Naoyuki Shimada; Bradley O Ashburn; Ashok K Basak; William F Bow; David A Vicic; Marcus A Tius
Journal:  Chem Commun (Camb)       Date:  2010-04-28       Impact factor: 6.222

4.  A facile synthesis of dibenzopyrroloazepinones as tetracyclic allocolchicinoids--an unusual 1,2-phenyl shift.

Authors:  Liang Wu; Abil E Aliev; Stephen Caddick; Richard J Fitzmaurice; Derek A Tocher; Frank D King
Journal:  Chem Commun (Camb)       Date:  2009-11-30       Impact factor: 6.222

5.  Discovery of (R)-9-ethyl-1,3,4,10b-tetrahydro-7-trifluoromethylpyrazino[2,1-a]isoindol- 6(2H)-one, a selective, orally active agonist of the 5-HT(2C) receptor.

Authors:  Dean A Wacker; Jeffrey G Varnes; Sarah E Malmstrom; Xueying Cao; Chen-Pin Hung; Thao Ung; Ginger Wu; Ge Zhang; Eva Zuvich; Michael A Thomas; William J Keim; Mary Jane Cullen; Kenneth W Rohrbach; Qinling Qu; Rangaraj Narayanan; Karen Rossi; Evan Janovitz; Lois Lehman-McKeeman; Mary F Malley; James Devenny; Mary Ann Pelleymounter; Keith J Miller; Jeffrey A Robl
Journal:  J Med Chem       Date:  2007-02-23       Impact factor: 7.446

6.  Enantioselective Brønsted acid-catalyzed N-acyliminium cyclization cascades.

Authors:  Michael E Muratore; Chloe A Holloway; Adam W Pilling; R Ian Storer; Graham Trevitt; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419

7.  A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation.

Authors:  Frank D King; Abil E Aliev; Stephen Caddick; Derek A Tocher; Denis Courtier-Murias
Journal:  Org Biomol Chem       Date:  2008-11-12       Impact factor: 3.876

8.  An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: a facile synthesis of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones.

Authors:  Frank D King; Abil E Aliev; Stephen Caddick; Royston C B Copley
Journal:  Org Biomol Chem       Date:  2009-07-09       Impact factor: 3.876

9.  Aza-Nazarov reaction and the role of superelectrophiles.

Authors:  Douglas A Klumpp; Yiliang Zhang; Matthew J O'Connor; Pierre M Esteves; Leonardo S de Almeida
Journal:  Org Lett       Date:  2007-07-14       Impact factor: 6.005

10.  Diketoacid-genre HIV-1 integrase inhibitors containing enantiomeric arylamide functionality.

Authors:  Xue Zhi Zhao; Kasthuraiah Maddali; Christophe Marchand; Yves Pommier; Terrence R Burke
Journal:  Bioorg Med Chem       Date:  2009-05-08       Impact factor: 3.641
  10 in total
  3 in total

1.  Rhodium catalyzed synthesis of isoindolinones via C-H activation of N-benzoylsulfonamides.

Authors:  Chen Zhu; John R Falck
Journal:  Tetrahedron       Date:  2012-09-04       Impact factor: 2.457

Review 2.  Superelectrophiles: Recent Advances.

Authors:  Douglas A Klumpp; Maksim V Anokhin
Journal:  Molecules       Date:  2020-07-19       Impact factor: 4.411

3.  Direct Synthesis of Enamides via Electrophilic Activation of Amides.

Authors:  Philipp Spieß; Martin Berger; Daniel Kaiser; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2021-07-07       Impact factor: 15.419
  3 in total

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