Literature DB >> 19603087

Domino Heck-Aza-Michael Reactions: A One-Pot, Sequential Three-Component Approach to 1,1-Dioxido-1,2-benzisothiazoline-3-acetic Acid.

Alan Rolfe1, Kyle Young, Paul R Hanson.   

Abstract

The development of a new method for the synthesis of 1,1-dioxido-1,2-benzisothiazoline-3-acetic acid by a domino process is reported whereby a classical Heck reaction is coupled to an intramolecular aza-Michael reaction. Ultimately, this method has been expanded to a one-pot, sequential three-component protocol to generate diverse benzofused γ-sultams from a range of commercially available α-bromobenzenesulfonyl chlorides, amines and Michael acceptors.

Entities:  

Year:  2008        PMID： 19603087      PMCID： PMC2709420          DOI： 10.1002/ejoc.200800651

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  31 in total

1.  Rhodium(II,II) dimer as an efficient catalyst for aziridination of sulfonamides and amidation of steroids.

Authors:  Jiang-Lin Liang; Shi-Xue Yuan; Philip Wai Hong Chan; Chi-Ming Che
Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

Review 2.  Synthesis of phosphorus and sulfur heterocycles via ring-closing olefin metathesis.

Authors:  Matthew D McReynolds; Joseph M Dougherty; Paul R Hanson
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

3.  Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes.

Authors:  Wei Zeng; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

4.  Microwave-assisted tandem cross metathesis intramolecular Aza-Michael reaction: an easy entry to cyclic beta-amino carbonyl derivatives.

Authors:  Santos Fustero; Diego Jiménez; María Sanchez-Roselló; Carlos del Pozo
Journal:  J Am Chem Soc       Date:  2007-05-05       Impact factor: 15.419

5.  Direct comparison of the response of bicyclic sultam and lactam dienes to photoexcitation. Concerning the propensity of differing bond types to bridgehead nitrogen for homolytic cleavage.

Authors:  Leo A Paquette; Robert D Dura; Nathan Fosnaugh; Marshall Stepanian
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

6.  Synthesis of cyclic sulfonamides through intramolecular Diels-Alder reactions.

Authors:  I R Greig; M J Tozer; P T Wright
Journal:  Org Lett       Date:  2001-02-08       Impact factor: 6.005

7.  Domino reactions that combine an azido-Schmidt ring expansion with the Diels-Alder reaction.

Authors:  Yibin Zeng; D Srinivasa Reddy; Erin Hirt; Jeffrey Aubé
Journal:  Org Lett       Date:  2004-12-23       Impact factor: 6.005

8.  Synthesis of 6-phenanthridinones and their heterocyclic analogues through palladium-catalyzed sequential aryl-aryl and N-aryl coupling.

Authors:  Raffaella Ferraccioli; Davide Carenzi; Ottavio Rombolà; Marta Catellani
Journal:  Org Lett       Date:  2004-12-09       Impact factor: 6.005

9.  Asymmetric aza-Michael reactions catalyzed by cinchona alkaloids.

Authors:  Dario Perdicchia; Karl Anker Jørgensen
Journal:  J Org Chem       Date:  2007-03-29       Impact factor: 4.354

10.  High-load, soluble oligomeric carbodiimide: synthesis and application in coupling reactions.

Authors:  Mianji Zhang; Punitha Vedantham; Daniel L Flynn; Paul R Hanson
Journal:  J Org Chem       Date:  2004-11-26       Impact factor: 4.354
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  15 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.  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.  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.  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.  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

6.  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

7.  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

8.  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

9.  One-pot, three-component, domino Heck-aza-Michael approach to libraries of functionalized 1,1-dioxido-1,2-benzisothiazoline-3-acetic acids.

Authors:  Alan Rolfe; Kyle Young; Kelly Volp; Frank Schoenen; Benjamin Neuenswander; Gerald H Lushington; Paul R Hanson
Journal:  J Comb Chem       Date:  2009 Jul-Aug

10.  "Click, click, cyclize": a DOS approach to sultams utilizing vinyl sulfonamide linchpins.

Authors:  Aihua Zhou; Dinesh Rayabarapu; Paul R Hanson
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005
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