Literature DB >> 20161276

α-Haloarylsulfonamides: Multiple Cyclization Pathways to Skeletally Diverse Benzofused Sultams.

Dinesh Kumar Rayabarapu1, Aihua Zhou, Kyu Ok Jeon, Thiwanka Samarakoon, Alan Rolfe, Hina Siddiqui, Paul R Hanson.   

Abstract

The development of new methods to skeletally diverse sultams based on a central α-halo benzene sulfonamide building block is reported. Several salient features of this building block are utilized in multiple reaction pathways, including the Heck reaction, C- and O-arylation, Sonogashira-Pauson-Khand, Sonogashira-intramolecular hydroamination, lithiative cyclization and domino aza-Michael Heck for the generation of 5-, 6- and 7-membered benzofused bicyclic and tricyclic sultams.

Entities:  

Year:  2009        PMID： 20161276      PMCID： PMC2702864          DOI： 10.1016/j.tet.2008.11.053

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  27 in total

1.  Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.

Authors:  Vincent Ritleng; Claude Sirlin; Michel Pfeffer
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

2.  Diversity-oriented synthesis; a challenge for synthetic chemists.

Authors:  David R Spring
Journal:  Org Biomol Chem       Date:  2003-11-21       Impact factor: 3.876

3.  Pyrrolo[1,2-b][1,2,5]benzothiadiazepines (PBTDs): A new class of agents with high apoptotic activity in chronic myelogenous leukemia K562 cells and in cells from patients at onset and who were imatinib-resistant.

Authors:  Romano Silvestri; Gabriella Marfè; Marino Artico; Giuseppe La Regina; Antonio Lavecchia; Ettore Novellino; Emanuela Morgante; Manuela Morgante; Carla Di Stefano; Gianfranco Catalano; Giuseppe Filomeni; Elisabetta Abruzzese; Maria Rosa Ciriolo; Matteo Antonio Russo; Sergio Amadori; Roberto Cirilli; Francesco La Torre; Paola Sinibaldi Salimei
Journal:  J Med Chem       Date:  2006-09-21       Impact factor: 7.446

4.  Synthesis of potential biologically active 1,2-benzothiazin-3-yl-quinazolin-4(3H)-ones.

Authors:  Muhammad Zia-ur-Rehman; Jamil Anwar Choudary; Saeed Ahmad; Hamid Latif Siddiqui
Journal:  Chem Pharm Bull (Tokyo)       Date:  2006-08       Impact factor: 1.645

5.  An approach to skeletal diversity using functional group pairing of multifunctional scaffolds.

Authors:  Eamon Comer; Erin Rohan; Li Deng; John A Porco
Journal:  Org Lett       Date:  2007-05-02       Impact factor: 6.005

6.  Diversity-oriented synthesis.

Authors:  Richard J Spandl; Mónica Díaz-Gavilán; Kieron M G O'Connell; Gemma L Thomas; David R Spring
Journal:  Chem Rec       Date:  2008       Impact factor: 6.771

7.  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

8.  Synthesis and anti-HIV-1 activity of a novel series of 1,4,2-benzodithiazine-dioxides.

Authors:  Zdzisław Brzozowski; Franciszek Saczewski; Nouri Neamati
Journal:  Bioorg Med Chem Lett       Date:  2006-08-14       Impact factor: 2.823

9.  1,2-Benzothiazine 1,1-dioxide P(2)-P(3) peptide mimetic aldehyde calpain I inhibitors.

Authors:  G J Wells; M Tao; K A Josef; R Bihovsky
Journal:  J Med Chem       Date:  2001-10-11       Impact factor: 7.446

10.  1,2,5-Benzothiadiazepine and pyrrolo[2,1-d]-[1,2,5]benzothiadiazepine derivatives with specific anti-human immunodeficiency virus type 1 activity.

Authors:  R Di Santo; R Costi; M Artico; S Massa; M E Marongiu; A G Loi; A De Montis; P La Colla
Journal:  Antivir Chem Chemother       Date:  1998-03
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  15 in total

1.  Synthesis of epoxybenzo[d]isothiazole 1,1-dioxides via a reductive-Heck, metathesis-sequestration protocol.

Authors:  Naeem Asad; Paul R Hanson; Toby R Long; Dinesh K Rayabarapu; Alan Rolfe
Journal:  Chem Commun (Camb)       Date:  2011-07-05       Impact factor: 6.222

2.  Discovery of sultam-containing small-molecule disruptors of the huntingtin-calmodulin protein-protein interaction.

Authors:  Nicholas J Klus; Khushboo Kapadia; Peter McDonald; Anuradha Roy; Kevin J Frankowski; Nancy A Muma; Jeffrey Aubé
Journal:  Med Chem Res       Date:  2020-06-12       Impact factor: 1.965

3.  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

4.  A formal [4 + 4] complementary ambiphile pairing reaction: a new cyclization pathway for ortho-quinone methides.

Authors:  Thiwanka B Samarakoon; Moon Y Hur; Ryan D Kurtz; Paul R Hanson
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

5.  An oxidation of benzyl methyl ethers with nbs that selectively affords either aromatic aldehydes or aromatic methyl esters.

Authors:  Abdelrahman S Mayhoub; Arindam Talukdar; Mark Cushman
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

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.  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.  A modular reaction pairing approach to the diversity-oriented synthesis of fused- and bridged-polycyclic sultams.

Authors:  Thiwanka B Samarakoon; Joanna K Loh; Alan Rolfe; Lisa S Le; Sun Young Yoon; Gerald H Lushington; Paul R Hanson
Journal:  Org Lett       Date:  2011-09-07       Impact factor: 6.005

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.  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
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