Literature DB >> 22311745

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

Qin Zang1, Salim Javed, Patrick Porubsky, Farman Ullah, Benjamin Neuenswander, Gerald H Lushington, Fatima Z Basha, Michael G Organ, Paul R Hanson.   

Abstract

The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1'-carbonyldiimidazole coupling generates a variety of tricyclic sultams. Overall, a 160-member library of these sultams, together with their isoindolines/THIQ and secondary sulfonamides precursors, were constructed using this strategy.

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Year:  2012        PMID： 22311745      PMCID： PMC3341135          DOI： 10.1021/co200181x

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


  37 in total

1.  Novel isoindoline compounds for potent and selective inhibition of prolyl dipeptidase DPP8.

Authors:  Weir-Torn Jiaang; Yuan-Shou Chen; Tsu Hsu; Ssu-Hui Wu; Chia-Hui Chien; Chung-Nien Chang; Sheng-Ping Chang; Shiow-Ju Lee; Xin Chen
Journal:  Bioorg Med Chem Lett       Date:  2005-02-01       Impact factor: 2.823

2.  Genomic sciences and the medicine of tomorrow.

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

3.  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

4.  DC-52, a novel antitumor antibiotic. 1. Taxonomy, fermentation and biological activity.

Authors:  F Tomita; K Takahashi; K Shimizu
Journal:  J Antibiot (Tokyo)       Date:  1983-05       Impact factor: 2.649

5.  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

6.  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

7.  Synthesis of non-proteinogenic phenylalanine derivatives by rhodium-catalyzed [2+2+2] cycloaddition reactions.

Authors:  Lídia Garcia; Anna Pla-Quintana; Anna Roglans
Journal:  Org Biomol Chem       Date:  2009-09-30       Impact factor: 3.876

8.  DC-52, a novel antitumor antibiotic. 2. Isolation, physico-chemical characteristics and structure determination.

Authors:  K Takahashi; F Tomita
Journal:  J Antibiot (Tokyo)       Date:  1983-05       Impact factor: 2.649

9.  Formation of pentacyclic structures by a domino sequence on cyclic enamides.

Authors:  Gedu Satyanarayana; Caecilia Maichle-Mössmer; Martin E Maier
Journal:  Chem Commun (Camb)       Date:  2009-01-30       Impact factor: 6.222

10.  SAR studies for a new class of antibacterial NAD biosynthesis inhibitors.

Authors:  Whitney Beysselance Moro; Zhengrong Yang; Tasha A Kane; Qingxian Zhou; Steve Harville; Christie G Brouillette; Wayne J Brouillette
Journal:  J Comb Chem       Date:  2009 Jul-Aug
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  7 in total

1.  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

2.  Rapid, scalable assembly of stereochemically rich, mono- and bicyclic acyl sultams.

Authors:  Naeem Asad; Thiwanka B Samarakoon; Qin Zang; Joanna K Loh; Salim Javed; Paul R Hanson
Journal:  Org Lett       Date:  2013-12-06       Impact factor: 6.005

3.  3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: Aza-Michael addition reactions and the preparation of poly-HOPO chelators.

Authors:  Gloria Martinez; Jayanthi Arumugam; Hollie K Jacobs; Aravamudan S Gopalan
Journal:  Tetrahedron Lett       Date:  2013-02-13       Impact factor: 2.415

4.  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

5.  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

6.  Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines.

Authors:  Anirudra Paul; Camille Vasseur; Scott D Daniel; Daniel Seidel
Journal:  Org Lett       Date:  2022-01-31       Impact factor: 6.072

Review 7.  Machine-Assisted Organic Synthesis.

Authors:  Steven V Ley; Daniel E Fitzpatrick; Rebecca M Myers; Claudio Battilocchio; Richard J Ingham
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-16       Impact factor: 15.336
  7 in total

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