Literature DB >> 22384820

Facile (triazolyl)methylation of MACOS-derived benzofused sultams utilizing ROMP-derived OTP reagents.

Saqib Faisal1, Farman Ullah, Pradip K Maity, Alan Rolfe, Thiwanka B Samarakoon, Patrick Porubsky, Benjamin Neuenswander, Gerald H Lushington, Fatima Z Basha, Michael G Organ, Paul R Hanson.   

Abstract

A combination of MACOS scale-out and ROMP-derived oligomeric triazole phosphates (OTP(n)) have been successfully utilized for the preparation of a 106-member library of triazole containing benzothiaoxazepine-1,1-dioxides. This report demonstrates the utilization of a suite of soluble OTP(n) reagents for facile (triazolyl)methylation of 10 MACOS-derived sultam scaffolds in purification-free process for parallel synthesis of small molecule collections for HTS.

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Year:  2012        PMID： 22384820      PMCID： PMC3656824          DOI： 10.1021/co2001839

Source DB:  PubMed          Journal:  ACS Comb Sci        ISSN： 2156-8944            Impact factor:   3.784


  38 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.  A fully automated, multistep flow synthesis of 5-amino-4-cyano-1,2,3-triazoles.

Authors:  Catherine J Smith; Nikzad Nikbin; Steven V Ley; Heiko Lange; Ian R Baxendale
Journal:  Org Biomol Chem       Date:  2011-01-31       Impact factor: 3.876

3.  S(N)Ar-based, facile synthesis of a library of benzothiaoxazepine-1,1'-dioxides.

Authors:  Alan Rolfe; Thiwanka B Samarakoon; Sarra V Klimberg; Marek Brzozowski; Benjamin Neuenswander; Gerald H Lushington; Paul R Hanson
Journal:  J Comb Chem       Date:  2010-09-29

4.  Organic synthesis: Scavengers in full flow.

Authors:  Peter H Seeberger
Journal:  Nat Chem       Date:  2009-07       Impact factor: 24.427

5.  Improving chemical synthesis using flow reactors.

Authors:  Charlotte Wiles; Paul Watts
Journal:  Expert Opin Drug Discov       Date:  2007-11       Impact factor: 6.098

6.  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

7.  Accessing Stereochemically Rich Sultams via Microwave-Assisted, Continuous Flow Organic Synthesis (MACOS) Scale-out.

Authors:  Michael G Organ; Paul R Hanson; Alan Rolfe; Thiwanka B Samarakoon; Farman Ullah
Journal:  J Flow Chem       Date:  2011-08       Impact factor: 2.786

8.  Application of a Double Aza-Michael Reaction in a 'Click, Click, Cy-Click' Strategy: From Bench to Flow.

Authors:  Qin Zang; Salim Javed; Farman Ullah; Aihua Zhou; Christopher A Knudtson; Danse Bi; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  Synthesis (Stuttg)       Date:  2011-09-01       Impact factor: 3.157

9.  Reagent based DOS: a "Click, Click, Cyclize" strategy to probe chemical space.

Authors:  Alan Rolfe; Gerald H Lushington; Paul R Hanson
Journal:  Org Biomol Chem       Date:  2010-03-16       Impact factor: 3.876

10.  Synthesis of a stereochemically diverse library of medium-sized lactams and sultams via S(N)Ar cycloetherification.

Authors:  Baudouin Gerard; Jeremy R Duvall; Jason T Lowe; Tiffanie Murillo; Jingqiang Wei; Lakshmi B Akella; Lisa A Marcaurelle
Journal:  ACS Comb Sci       Date:  2011-04-28       Impact factor: 3.784
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  4 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
  4 in total

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