Literature DB >> 24675905

Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N'-dimethylhydrazine dihydrochloride.

Zhiwei Yin1, Jinzhu Zhang, Jing Wu, Riana Green, Sihan Li, Shengping Zheng.   

Abstract

An unexpected nucleophilic chlorination of a quinone monoketal while carrying out a pyrazolidine synthesis has led to a general preparation of multisubstituted phenols. The products are obtained in good to high yields under mild conditions. The bridged pyrazolidines that were the original targets are obtained in the presence of a protic solvent.

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Year:  2014        PMID： 24675905      PMCID： PMC4075316          DOI： 10.1039/c4ob00391h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  24 in total

1.  Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis.

Authors:  D Magdziak; S J Meek; T R R Pettus
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

2.  New cyclohexadienone derivatives: preparation and chiral discrimination in high-pressure Diels-Alder cycloadditions.

Authors:  M E Trân-Huu-Dâu; R Wartchow; E Winterfeldt; Y S Wong
Journal:  Chemistry       Date:  2001-06-01       Impact factor: 5.236

3.  Synthesis and biological evaluation of ABCD ring fragments of the kibdelones.

Authors:  David L Sloman; Branko Mitasev; Stephen S Scully; John A Beutler; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-18       Impact factor: 15.336

4.  Efficient synthesis of oxygenated terphenyls and other oligomers: sequential arylation reactions through phenol oxidation-rearomatization.

Authors:  Toshifumi Dohi; Tohru Kamitanaka; Shohei Watanabe; Yinjun Hu; Naohiko Washimi; Yasuyuki Kita
Journal:  Chemistry       Date:  2012-09-20       Impact factor: 5.236

5.  A variation of the Fischer indolization involving condensation of quinone monoketals and aliphatic hydrazines.

Authors:  Jinzhu Zhang; Zhiwei Yin; Patrick Leonard; Jing Wu; Kate Sioson; Che Liu; Robert Lapo; Shengping Zheng
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-02       Impact factor: 15.336

6.  Total synthesis of the quinone epoxide dimer (+)-torreyanic acid: application of a biomimetic oxidation/electrocyclization/Diels-Alder dimerization cascade.

Authors:  Chaomin Li; Richard P Johnson; John A Porco
Journal:  J Am Chem Soc       Date:  2003-04-30       Impact factor: 15.419

7.  Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine.

Authors:  Scott Grecian; Jeffrey Aubé
Journal:  Org Lett       Date:  2007-07-12       Impact factor: 6.005

8.  Hypervalent iodine mediated synthesis of carbamate protected p-quinone monoimine ketals and p-benzoquinone monoketals.

Authors:  Naganjaneyulu Bodipati; Rama Krishna Peddinti
Journal:  Org Biomol Chem       Date:  2012-05-08       Impact factor: 3.876

9.  Metal-free oxidation of aromatic carbon-hydrogen bonds through a reverse-rebound mechanism.

Authors:  Changxia Yuan; Yong Liang; Taylor Hernandez; Adrian Berriochoa; Kendall N Houk; Dionicio Siegel
Journal:  Nature       Date:  2013-07-11       Impact factor: 49.962

10.  A direct route to fluostatin C by a fascinating Diels-Alder reaction.

Authors:  Maolin Yu; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-02-07       Impact factor: 15.419
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