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Literature DB >> 30840455

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

Jason V Chari¹, Francesca M Ippoliti¹, Neil K Garg¹.

Abstract

Silyl triflate precursors to cyclic alkynes and allenes serve as valuable synthetic building blocks. We report a concise and scalable synthetic approach to prepare the silyl triflate precursors to cyclohexyne and 1,2-cyclohexadiene. The strategy involves a retro-Brook rearrangement of an easily accessible cyclohexanone derivative, followed by triflation protocols. This simple, yet controlled, method should enable the further study of strained alkynes and allenes in chemical synthesis.

Entities: Chemical Disease Gene

Mesh：

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Year: 2019 PMID： 30840455 PMCID： PMC6935045 DOI： 10.1021/acs.joc.8b03223

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

35 in total

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2. Enabling the use of heterocyclic arynes in chemical synthesis.

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3. Synthesis, transformation, and general pharmacologic activity in 1,4-benzodiazepine-3,5-diones.

Authors: N D Heindel; W P Fives; T F Lemke; J E Rowe; H W Snady
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4. Strained Allenes as Dienophiles in the Diels-Alder Reaction: An Experimental and Computational Study.

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5. Synthesis and nicotinic acetylcholine receptor binding properties of bridged and fused ring analogues of epibatidine.

Authors: F Ivy Carroll; T Philip Robinson; Lawrence E Brieaddy; Robert N Atkinson; S Wayne Mascarella; M Imad Damaj; Billy R Martin; Hernán A Navarro
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Review 6. Aryne-based strategy in the total synthesis of naturally occurring polycyclic compounds.

Authors: Hiroshi Takikawa; Arata Nishii; Takahiro Sakai; Keisuke Suzuki
Journal: Chem Soc Rev Date: 2018-10-29 Impact factor: 54.564

7. Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline.

Authors: P Jacob; A T Shulgin
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8. Conjugated Trimeric Scaffolds Accessible from Indolyne Cyclotrimerizations: Synthesis, Structures, and Electronic Properties.

Authors: Janice B Lin; Tejas K Shah; Adam E Goetz; Neil K Garg; K N Houk
Journal: J Am Chem Soc Date: 2017-07-18 Impact factor: 15.419

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

1. Total syntheses of guanacastepenes N and O.

2. Enabling the use of heterocyclic arynes in chemical synthesis.

3. Synthesis, transformation, and general pharmacologic activity in 1,4-benzodiazepine-3,5-diones.

4. Strained Allenes as Dienophiles in the Diels-Alder Reaction: An Experimental and Computational Study.

5. Synthesis and nicotinic acetylcholine receptor binding properties of bridged and fused ring analogues of epibatidine.

Review 6. Aryne-based strategy in the total synthesis of naturally occurring polycyclic compounds.

7. Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline.

8. Conjugated Trimeric Scaffolds Accessible from Indolyne Cyclotrimerizations: Synthesis, Structures, and Electronic Properties.

9. Efficient Trapping of 1,2-Cyclohexadienes with 1,3-Dipoles.

10. Cycloadditions of cyclohexynes and cyclopentyne.

1. 1,2-Bis(arylthio)arene synthesis via aryne intermediates.

2. Origins of Endo Selectivity in Diels-Alder Reactions of Cyclic Allene Dienophiles.