Literature DB >> 11772110

Novel 1,4-benzodiazepines from acylnitroso-derived hetero-Diels-Alder cycloadducts.

Matthew D Surman1, Mark J Mulvihill, Marvin J Miller.   

Abstract

[reaction: see text] N(4)-Hydroxy-1,4-benzodiazepines were synthesized in a single step from synthetically versatile acylnitroso-derived hetero-Diels-Alder cycloadducts. The efficiency of this transformation was found to be dependent on the NH pK(a) of the cycloadduct sulfonamide.

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Year:  2002        PMID： 11772110     DOI： 10.1021/ol017036w

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


  11 in total

1.  Pd(0)/InI-mediated allylic additions to 4-acetoxy-2-azetidinone: new route to highly functionalized carbocyclic scaffolds.

Authors:  Cara Cesario; Marvin J Miller
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

2.  Expanding the results of a high throughput screen against an isochorismate-pyruvate lyase to enzymes of a similar scaffold or mechanism.

Authors:  Kathleen M Meneely; Qianyi Luo; Andrew P Riley; Byron Taylor; Anuradha Roy; Ross L Stein; Thomas E Prisinzano; Audrey L Lamb
Journal:  Bioorg Med Chem       Date:  2014-09-16       Impact factor: 3.641

3.  Regio- and stereochemically controlled formation of hydroxamic acids from indium triflate-mediated nucleophilic ring-opening reactions with acylnitroso-Diels-Alder adducts.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-02-10       Impact factor: 2.415

4.  Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside.

Authors:  Cheng Ji; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2010-07-01       Impact factor: 2.415

Review 5.  The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-21       Impact factor: 15.336

6.  Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct.

Authors:  Weiqiang Huang; Marvin J Miller
Journal:  Tetrahedron Asymmetry       Date:  2008-12-12

7.  Titanocene(III) chloride-mediated reductions of oxazines, hydroxamic acids, and N-hydroxy carbamates.

Authors:  Cara Cesario; Lawrence P Tardibono; Marvin J Miller
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354

8.  Regio- and stereoselective indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

9.  Synthesis and anticancer activity of new hydroxamic acid containing 1,4-benzodiazepines.

Authors:  Lawrence P Tardibono; Marvin J Miller
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

10.  Reactions of nitroso hetero-Diels-Alder cycloadducts with azides: stereoselective formation of triazolines and aziridines.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  J Org Chem       Date:  2007-04-13       Impact factor: 4.354
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