Literature DB >> 22027744

Intramolecular monomer-on-monomer (MoM) Mitsunobu cyclization for the synthesis of benzofused thiadiazepine-dioxides.

Pradip K Maity1, Quirin M Kainz, Saqib Faisal, Alan Rolfe, Thiwanka B Samarakoon, Fatima Z Basha, Oliver Reiser, Paul R Hanson.   

Abstract

The utilization of a monomer-on-monomer (MoM) intramolecular Mitsunobu cyclization reaction employing norbornenyl-tagged (Nb-tagged) reagents is reported for the synthesis of benzofused thiadiazepine-dioxides. Facile purification was achieved via ring-opening metathesis (ROM) polymerization initiated by one of three metathesis catalyst methods: (i) free metathesis catalyst, (ii) surface-initiated catalyst-armed silica, or (iii) surface-initiated catalyst-armed Co/C magnetic nanoparticles.

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Year:  2011        PMID： 22027744      PMCID： PMC3271939          DOI： 10.1039/c1cc14807a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  34 in total

1.  Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy.

Authors:  Alan Rolfe; Thiwanka B Samarakoon; Paul R Hanson
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

2.  Mitsunobu and related reactions: advances and applications.

Authors:  K C Kumara Swamy; N N Bhuvan Kumar; E Balaraman; K V P Pavan Kumar
Journal:  Chem Rev       Date:  2009-06       Impact factor: 60.622

3.  Utilizing the intramolecular Fukuyama-Mitsunobu reaction for a flexible synthesis of novel heterocyclic scaffolds for peptidomimetic drug design.

Authors:  Christoph W Zapf; Juan R Del Valle; Murray Goodman
Journal:  Bioorg Med Chem Lett       Date:  2005-09-15       Impact factor: 2.823

4.  High-load, hybrid Si-ROMP reagents.

Authors:  Alan Rolfe; Joanna K Loh; Pradip K Maity; Paul R Hanson
Journal:  Org Lett       Date:  2010-12-01       Impact factor: 6.005

5.  Polyisobutylene-supported phosphines as recyclable and regenerable catalysts and reagents.

Authors:  David E Bergbreiter; Yun-Chin Yang; Christopher E Hobbs
Journal:  J Org Chem       Date:  2011-07-12       Impact factor: 4.354

6.  Impurity annihilation: chromatography-free parallel Mitsunobu reactions.

Authors:  A G Barrett; R S Roberts; J Schröder
Journal:  Org Lett       Date:  2000-09-21       Impact factor: 6.005

7.  Multipolymer solution-phase reactions: application to the Mitsunobu reaction.

Authors:  Andrew M Harned; Helen Song He; Patrick H Toy; Daniel L Flynn; Paul R Hanson
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

8.  Enantioselective total synthesis of (+)-dibromophakellstatin.

Authors:  Karine G Poullennec; Daniel Romo
Journal:  J Am Chem Soc       Date:  2003-05-28       Impact factor: 15.419

9.  Chemically-tagged Mitsunobu reagents for use in solution-phase chemical library synthesis.

Authors:  G W Starkey; J J Parlow; D L Flynn
Journal:  Bioorg Med Chem Lett       Date:  1998-09-08       Impact factor: 2.823

10.  Selectively N-protected enantiopure 2,5-disubstituted piperazines: avoiding the pitfalls in solid-phase Fukuyama-Mitsunobu cyclizations.

Authors:  Lars K Ottesen; Christian A Olsen; Matthias Witt; Jerzy W Jaroszewski; Henrik Franzyk
Journal:  Chemistry       Date:  2009       Impact factor: 5.236
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  5 in total

1.  Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents.

Authors:  Pradip K Maity; Saqib Faisal; Alan Rolfe; Diana Stoianova; Paul R Hanson
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

2.  Development and Application of a Recyclable High-Load Magnetic Co/C Hybrid ROMP-Derived Benzenesulfonyl Chloride Reagent and Utility of Corresponding Analogues.

Authors:  Saqib Faisal; Qin Zang; Pradip K Maity; Agnes Brandhofer; Patrick C Kearney; Oliver Reiser; Robert N Grass; Diana Stoianova; Paul R Hanson
Journal:  Org Lett       Date:  2017-04-24       Impact factor: 6.005

3.  Synthesis of High-Load, Hybrid Silica-Immobilized Heterocyclic Benzyl Phosphate (Si-OHBP) and Triazolyl Phosphate (Si-OHTP) Alkylating Reagents.

Authors:  Saqib Faisal; Pradip K Maity; Qin Zang; Alan Rolfe; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2016-06-14       Impact factor: 3.784

4.  Application of Silica-Supported Alkylating Reagents in a One-Pot, Sequential Protocol to Diverse Benzoxathiazepine 1,1-Dioxides.

Authors:  Saqib Faisal; Pradip K Maity; Qin Zang; Thiwanka B Samarakoon; Robert L Sourk; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2016-06-14       Impact factor: 3.784

5.  Magnetic Nanobeads as Support for Zinc(II)-Cyclen Complexes: Selective and Reversible Extraction of Riboflavin.

Authors:  Quirin M Kainz; Andreas Späth; Stefan Weiss; Thomas D Michl; Alexander Schätz; Wendelin J Stark; Burkhard König; Oliver Reiser
Journal:  ChemistryOpen       Date:  2012-06-11       Impact factor: 2.911
  5 in total

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