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Literature DB >> 19505109

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

Alan Rolfe¹, Kyle Young, Kelly Volp, Frank Schoenen, Benjamin Neuenswander, Gerald H Lushington, Paul R Hanson.

Abstract

A sequential three-component synthesis of functionalized benzisothiazoline-3-acetic acid 1,1-dioxides utilizing a domino Heck-aza-Michael pathway is reported. This one-pot procedure rapidly assembles functionalized benzylsulfonamides, which undergo a palladium-catalyzed, domino, Heck-aza-Michael transformation in an experimentally straightforward manner. This attractive protocol has been utilized to synthesize three combinatorial sublibraries (I-III) comprising a total of 95 compounds in high purities (> or =95% for 75 compounds), yield and quantities.

Entities: Chemical Disease Species

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Year: 2009 PMID： 19505109 PMCID： PMC2895961 DOI： 10.1021/cc900025e

Source DB: PubMed Journal: J Comb Chem ISSN： 1520-4766

29 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. 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

4. Synthesis, antimycobacterial and antitumor activities of new (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl N,N-disubstituted dithiocarbamate/O-alkyldithiocarbonate derivatives.

Authors: Ozlen Güzel; Aydin Salman
Journal: Bioorg Med Chem Date: 2006-08-22 Impact factor: 3.641

5. 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

6. 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

7. 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

8. Catalytic asymmetric phase-transfer Michael reaction and Mannich-type reaction of glycine Schiff bases with tartrate-derived diammonium salts.

Authors: Tomoyuki Shibuguchi; Hisashi Mihara; Akiyoshi Kuramochi; Takashi Ohshima; Masakatsu Shibasaki
Journal: Chem Asian J Date: 2007-06-04

9. Aza-Michael addition of nosyloxycarbamates to 2-(trifluoromethyl)acrylates.

Authors: Daniele Colantoni; Stefania Fioravanti; Lucio Pellacani; Paolo A Tardella
Journal: Org Lett Date: 2004-01-22 Impact factor: 6.005

10. Tandem Pd-catalyzed double C-C bond formation: effect of water.

Authors: David I Chai; Mark Lautens
Journal: J Org Chem Date: 2009-04-17 Impact factor: 4.354

10 in total

Review 1. Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors: Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal: J Comb Chem Date: 2010-10-05

2. 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

3. 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

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. 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

6. 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

7. Scaling out by microwave-assisted, continuous flow organic synthesis (MACOS): multi-gram synthesis of bromo- and fluoro-benzofused sultams benzthiaoxazepine-1,1-dioxides.

Authors: Farman Ullah; Thiwanka Samarakoon; Alan Rolfe; Ryan D Kurtz; Paul R Hanson; Michael G Organ
Journal: Chemistry Date: 2010-09-24 Impact factor: 5.236