Literature DB >> 21902243

Synthesis of amino-benzothiaoxazepine-1,1-dioxides utilizing a microwave-assisted, S(N)Ar protocol.

Alan Rolfe1, Farman Ullah, Thiwanka B Samarakoon, Ryan D Kurtz, Patrick Porubsky, Benjamin Neuenswander, Gerald H Lushington, Conrad Santini, Michael G Organ, Paul R Hanson.   

Abstract

The development of a microwave-assisted, intermolecular S(N)Ar protocol for the synthesis of a 126-member benzothiaoxazepine-1,1-dioxide library is reported. Diversification of 12 benzothiaoxazepine-1,1-dioxides was achieved in rapid fashion utilizing a variety of 2° amines and amino alcohols to generate an 80-member library. A second 48-member library was subsequently generated via a two-step alkylation, intermolecular S(N)Ar diversification protocol.

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Year:  2011        PMID： 21902243      PMCID： PMC3271943          DOI： 10.1021/co200076j

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


  36 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 microreactor for microwave-assisted capillary (continuous flow) organic synthesis.

Authors:  Eamon Comer; Michael G Organ
Journal:  J Am Chem Soc       Date:  2005-06-08       Impact factor: 15.419

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.  Microwave-assisted sequential one-pot protocol to benzothiadiazin-3-one-1,1-dioxides via a copper-catalyzed N-arylation strategy.

Authors:  Alan Rolfe; Paul R Hanson
Journal:  Tetrahedron Lett       Date:  2009-12-16       Impact factor: 2.415

5.  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

6.  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

7.  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

8.  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

9.  Metathesis Cascade Strategies (ROM-RCM-CM): A DOS approach to Skeletally Diverse Sultams.

Authors:  Kyu Ok Jeon; Dinesh Rayabarapu; Alan Rolfe; Kelly Volp; Iman Omar; Paul R Hanson
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

10.  Pd PEPPSI-IPr-mediated reactions in metal-coated capillaries under MACOS: the synthesis of indoles by sequential aryl amination/Heck coupling.

Authors:  Gjergji Shore; Sylvie Morin; Debasis Mallik; Michael G Organ
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
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  5 in total

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

Authors:  Saqib Faisal; 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
Journal:  ACS Comb Sci       Date:  2012-03-05       Impact factor: 3.784

2.  Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS).

Authors:  Farman Ullah; Qin Zang; Salim Javed; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Paul R Hanson; Michael G Organ
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

3.  Multicapillary Flow Reactor: Synthesis of 1,2,5-Thiadiazepane 1,1-Dioxide Library Utilizing One-Pot Elimination and Inter-/Intramolecular Double aza-Michael Addition Via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS).

Authors:  Farman Ullah; Qin Zang; Salim Javed; Aihua Zhou; Christopher A Knudtson; Danse Bi; Paul R Hanson; Michael G Organ
Journal:  J Flow Chem       Date:  2012-12       Impact factor: 2.786

4.  Exploring chemical diversity via a modular reaction pairing strategy.

Authors:  Joanna K Loh; Sun Young Yoon; Thiwanka B Samarakoon; Alan Rolfe; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Paul R Hanson
Journal:  Beilstein J Org Chem       Date:  2012-08-15       Impact factor: 2.883

5.  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 in total

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