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Literature DB >> 28277580

Tandem 1,6-addition/cyclization/vinylcyclopropane rearrangement at low temperature under metal-free conditions: an approach to spiro[4.5]cyclohexadienones.

Zhenbo Yuan¹, Kuo Gai, Youzhi Wu, Jie Wu, Aijun Lin, Hequan Yao.

Abstract

A tandem 1,6-addition/cyclization/vinylcyclopropane rearrangement reaction (VCPR) of vinylogous para-quinone methides at low temperature under metal-free conditions has been disclosed for the first time. This method provides an efficient strategy for the construction of a range of spiro[4.5]cyclohexadienones in good yield, exhibiting good functional group tolerance as well as gram-scale capacity.

Entities: Chemical

Year: 2017 PMID： 28277580 DOI： 10.1039/c7cc00677b

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

5 in total

1. CF₃-Containing para-Quinone Methides for Organic Synthesis.

Authors: Michael Winter; Roman Schütz; Andreas Eitzinger; Armin R Ofial; Mario Waser
Journal: European J Org Chem Date: 2020-03-06

2. Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group.

Authors: Chuanhua Qu; Run Huang; Yong Li; Tong Liu; Yuan Chen; Guiting Song
Journal: Beilstein J Org Chem Date: 2021-12-02 Impact factor: 2.883

Tandem 1,6-addition/cyclization/vinylcyclopropane rearrangement at low temperature under metal-free conditions: an approach to spiro[4.5]cyclohexadienones.

1. CF₃-Containing para-Quinone Methides for Organic Synthesis.

2. Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group.

3. One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides.

4. Formal (4+1)-Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides.

5. Electrophilic Reactivities of Vinyl p-Quinone Methides.

Tandem 1,6-addition/cyclization/vinylcyclopropane rearrangement at low temperature under metal-free conditions: an approach to spiro[4.5]cyclohexadienones.

1. CF3-Containing para-Quinone Methides for Organic Synthesis.

2. Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group.

3. One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides.

4. Formal (4+1)-Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides.

5. Electrophilic Reactivities of Vinyl p-Quinone Methides.

1. CF₃-Containing para-Quinone Methides for Organic Synthesis.