Literature DB >> 21927510

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

Qin Zang1, Salim Javed, Farman Ullah, Aihua Zhou, Christopher A Knudtson, Danse Bi, Fatima Z Basha, Michael G Organ, Paul R Hanson.   

Abstract

The development of a 'click, click, cy-click' process utilizing a double aza-Michael reaction to generate functionalized 1,2,5-thiadiazepane 1,1-dioxides is reported. Optimization in flow, followed by scale out of the inter-/intramolecular double aza-Michael addition has also been realized using a microwave-assisted, continuous flow organic synthesis platform (MACOS). In addition, a facile one-pot, sequential strategy employing in situ Huisgen cycloaddition post-double aza-Michael has been accomplished, and is applicable to library synthesis.

Entities:  

Year:  2011        PMID： 21927510      PMCID： PMC3171749          DOI： 10.1055/s-0030-1260112

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  55 in total

1.  Organocatalytic asymmetric sulfa-michael/michael addition reactions: a strategy for the synthesis of highly substituted chromans with a quaternary stereocenter.

Authors:  Xu-Fan Wang; Qiu-Lin Hua; Ying Cheng; Xiao-Lei An; Qing-Qing Yang; Jia-Rong Chen; Wen-Jing Xiao
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-02       Impact factor: 15.336

2.  Stereocontrolled solid-phase synthesis of a 90-membered library of indoline-alkaloid-like polycycles from an enantioenriched aminoindoline scaffold.

Authors:  Zhonghong Gan; P Thirupathi Reddy; Sophie Quevillon; Samuel Couve-Bonnaire; Prabhat Arya
Journal:  Angew Chem Int Ed Engl       Date:  2005-02-18       Impact factor: 15.336

3.  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

4.  Cyclic anhydrides in formal cycloadditions and multicomponent reactions.

Authors:  Marcos González-López; Jared T Shaw
Journal:  Chem Rev       Date:  2009-01       Impact factor: 60.622

5.  Enantioselective organocatalytic domino oxa-Michael/aldol/hemiacetalization: synthesis of polysubstituted furofuranes containing four stereocenters.

Authors:  Efraím Reyes; Garazi Talavera; Jose L Vicario; Dolores Badía; Luisa Carrillo
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Genomic sciences and the medicine of tomorrow.

Authors:  J Drews
Journal:  Nat Biotechnol       Date:  1996-11       Impact factor: 54.908

7.  Stereoselective synthesis of 2,6-cis- and 2,6-trans-piperidines through organocatalytic aza-Michael reactions: a facile synthesis of (+)-myrtine and (-)-epimyrtine.

Authors:  Yongcheng Ying; Hyoungsu Kim; Jiyong Hong
Journal:  Org Lett       Date:  2011-01-20       Impact factor: 6.005

8.  Tandem asymmetric Michael reaction-intramolecular Michael addition. An easy entry to chiral fluorinated 1,4-dihydropyridines.

Authors:  Santos Fustero; Silvia Catalán; María Sánchez-Roselló; Antonio Simón-Fuentes; Carlos del Pozo
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

9.  Domino Heck-aza-Michael reactions: efficient access to 1-substituted tetrahydro-beta-carbolines.

Authors:  Daniel L Priebbenow; Luke C Henderson; Frederick M Pfeffer; Scott G Stewart
Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

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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  9 in total

1.  A summary of seven- and eight-membered ring sultam syntheses via three Michael addition reactions.

Authors:  Ben Niu; Ping Xie; Min Wang; Yanjie Wang; Wannian Zhao; Charles U Pittman; Aihua Zhou
Journal:  Mol Divers       Date:  2015-04-03       Impact factor: 2.943

2.  Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy.

Authors:  Qin Zang; Salim Javed; Patrick Porubsky; Farman Ullah; Benjamin Neuenswander; Gerald H Lushington; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2012-02-06       Impact factor: 3.784

3.  Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol.

Authors:  Qin Zang; Aihua Zhou; Salim Javed; Pradip K Maity; Chris A Knudtson; Danse Bi; Jared J Hastings; Fatima Z Basha; Paul R Hanson
Journal:  Heterocycles       Date:  2012-12-31       Impact factor: 0.831

4.  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

5.  Triazole-containing isothiazolidine 1,1-dioxide library synthesis: one-pot, multi-component protocols for small molecular probe discovery.

Authors:  Alan Rolfe; Thomas O Painter; Naeem Asad; Moon Young Hur; Kyu Ok Jeon; Marek Brzozowski; Sarra V Klimberg; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2011-08-25       Impact factor: 3.784

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

Authors:  Alan Rolfe; Farman Ullah; Thiwanka B Samarakoon; Ryan D Kurtz; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2011-09-08       Impact factor: 3.784

7.  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

8.  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

9.  Automated synthesis of a library of triazolated 1,2,5-thiadiazepane 1,1-dioxides via a double aza-Michael strategy.

Authors:  Qin Zang; Salim Javed; David Hill; Farman Ullah; Danse Bi; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2012-08-01       Impact factor: 3.784
  9 in total

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