Literature DB >> 19096499

Synthesis of 1,4-dihydro-benzo[d][1,3]oxazin-2-ones from phthalides via an aminolysis-Hofmann rearrangement protocol.

Eliud Hernández1, Jessica M Vélez, Cornelis P Vlaar.   

Abstract

A simple two-step procedure for the conversion of readily available phthalides to the corresponding benzoxazinones was developed. Initial ring-opening aminolysis to form a primary 2-hydroxymethylbenzamide, followed by reaction with bis(trifluoroacetoxy)iodobenzene (BTI) conveniently provided a variety of 4-substituted benzoxazinones.

Entities:  

Year:  2007        PMID： 19096499      PMCID： PMC2194645          DOI： 10.1016/j.tetlet.2007.10.114

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


  5 in total

Review 1.  Recent developments in the chemistry of polyvalent iodine compounds.

Authors:  Viktor V Zhdankin; Peter J Stang
Journal:  Chem Rev       Date:  2002-07       Impact factor: 60.622

2.  Efficient synthesis of isobenzofuran-1(3H)-ones (phthalides) and selected biological evaluations.

Authors:  Ernst Bayer; Safdar Hayat; M Iqbal Choudhary; Khalid Mohammed Khan; Syed Tasadaque Ali Shah; M Imran-ul-Haq; M Usman Anwar; Wolfgang Voelter
Journal:  Arzneimittelforschung       Date:  2005

3.  SAR studies of 6-(arylamino)-4,4-disubstituted-1-methyl-1,4-dihydro-benzo[d][1,3]oxazin-2-ones as progesterone receptor antagonists.

Authors:  Jeffrey C Kern; Eugene A Terefenko; Andrew Fensome; Ray Unwallla; Jay Wrobel; Yuan Zhu; Jeffrey Cohen; Richard Winneker; Zhiming Zhang; Puwen Zhang
Journal:  Bioorg Med Chem Lett       Date:  2006-10-05       Impact factor: 2.823

4.  Synthesis and evaluation of analogs of Efavirenz (SUSTIVA) as HIV-1 reverse transcriptase inhibitors.

Authors:  M Patel; S S Ko; R J McHugh; J A Markwalder; A S Srivastava; B C Cordova; R M Klabe; S Erickson-Viitanen; G L Trainor; S P Seitz
Journal:  Bioorg Med Chem Lett       Date:  1999-10-04       Impact factor: 2.823

5.  Synthesis and structure-activity relationship of novel 6-aryl-1,4-dihydrobenzo[d][1,3]oxazine-2-thiones as progesterone receptor modulators leading to the potent and selective nonsteroidal progesterone receptor agonist tanaproget.

Authors:  Andrew Fensome; Reinhold Bender; Rajiv Chopra; Jeff Cohen; Mark A Collins; Valerie Hudak; Karl Malakian; Susan Lockhead; Andrea Olland; Kristine Svenson; Eugene A Terefenko; Ray J Unwalla; James M Wilhelm; Scott Wolfrom; Yuan Zhu; Zhiming Zhang; Puwen Zhang; Richard C Winneker; Jay Wrobel
Journal:  J Med Chem       Date:  2005-08-11       Impact factor: 7.446
  5 in total
  3 in total

Review 1.  Recent advancements in synthetic methodologies of 3-substituted phthalides and their application in the total synthesis of biologically active natural products.

Authors:  Amardeep Awasthi; Mandeep Singh; Garima Rathee; Ramesh Chandra
Journal:  RSC Adv       Date:  2020-03-27       Impact factor: 4.036

2.  An Entry to Enantioenriched 3,3-Disubstituted Phthalides through Asymmetric Phase-Transfer-Catalyzed γ-Alkylation.

Authors:  Marina Sicignano; Rosaria Schettini; Giovanni Pierri; Maria Leda Marino; Irene Izzo; Francesco De Riccardis; Luca Bernardi; Giorgio Della Sala
Journal:  J Org Chem       Date:  2020-05-27       Impact factor: 4.354

3.  Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones.

Authors:  Marie Vayer; Miryam Pastor; Christiane Kofink; Nuno Maulide
Journal:  Org Lett       Date:  2021-12-24       Impact factor: 6.005
  3 in total

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