Literature DB >> 25328003

N-tosyl-3-azacyclohexyne. Synthesis and chemistry of a strained cyclic ynamide.

Sami F Tlais1, Rick L Danheiser.   

Abstract

The first synthesis of a strained six-membered cyclic ynamide is described. N-Tosyl-3-azacyclohexyne is generated via fluoride-promoted 1,2 elimination under conditions that allow trapping of the strained heterocyclic alkyne in a variety of addition, insertion, and [2 + 2], [3 + 2], and [4 + 2] cycloaddition reactions.

Entities:  

Year:  2014        PMID： 25328003     DOI： 10.1021/ja509055r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  9 in total

1.  Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors.

Authors:  Jason V Chari; Francesca M Ippoliti; Neil K Garg
Journal:  J Org Chem       Date:  2019-03-06       Impact factor: 4.354

2.  Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

Authors:  Tejas K Shah; Jose M Medina; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

3.  Nitrone Cycloadditions of 1,2-Cyclohexadiene.

Authors:  Joyann S Barber; Evan D Styduhar; Hung V Pham; Travis C McMahon; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-02-18       Impact factor: 15.419

4.  Silyl Tosylate Precursors to Cyclohexyne, 1,2-Cyclohexadiene, and 1,2-Cycloheptadiene.

Authors:  Matthew S McVeigh; Andrew V Kelleghan; Michael M Yamano; Rachel R Knapp; Neil K Garg
Journal:  Org Lett       Date:  2020-05-21       Impact factor: 6.005

5.  Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds.

Authors:  Evan R Darzi; Joyann S Barber; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-30       Impact factor: 15.336

6.  Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.

Authors:  Travis C McMahon; Jose M Medina; Yun-Fang Yang; Bryan J Simmons; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2015-03-20       Impact factor: 15.419

7.  Synthesis and Utilization of Nitroalkyne Equivalents in Batch and Continuous Flow.

Authors:  Peter D Morse; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-04       Impact factor: 15.336

8.  Ring Expansion of Alkylidenecarbenes Derived from Lactams, Lactones, and Thiolactones into Strained Heterocyclic Alkynes: A Theoretical Study.

Authors:  Nguyen Nhat Thu Le; Josefine Just; Jonathan M Pankauski; Paul R Rablen; Dasan M Thamattoor
Journal:  Molecules       Date:  2019-02-07       Impact factor: 4.411

Review 9.  Leveraging Fleeting Strained Intermediates to Access Complex Scaffolds.

Authors:  Sarah M Anthony; Laura G Wonilowicz; Matthew S McVeigh; Neil K Garg
Journal:  JACS Au       Date:  2021-06-23
  9 in total

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