Literature DB >> 26689538

Michael Reaction of 3-aAryl-2,4-Dicarboethoxy-5-Hydroxy-5-Methylcyclohexanones.

Fawzia Zakaria El-Ablack1, M A Metwally2, A M Khalil2.   

Abstract

The reaction of 3-aryl-2,4-dicarboethoxy-5-hydroxy-5-methylcyclohexanones 1with benzalacetone, dibenzalacetone, benzalacetophenone, and 4-benzal-1-phenyl-3-methyl pyrazolone has been investigated to give Michael compounds 2-5. hydrolysis of the dioxo derivative 4 afforded1,5-dicarbonyl derivative 6which On condensation with hydrazine and/or substituted hydrazine and hydroxylamine produced1,2-diazepine and 1,2-oxazepine derivatives 7,8 respectively. Reaction of β-Keto ester 1 with 1,3-diphenylacetone afforded 9. The structures of the hitherto unknown compounds have been confirmed by analytical and spectral data. The newly synthesized compounds have been screened to test their antimicrobial and antifungal activity.

Entities:  

Keywords:  1,2-diazepine; 1,2-oxazepine; Michael addition; Michael adduct; and antifungal activity; antibacterial; dioxo

Year:  2015        PMID: 26689538

Source DB:  PubMed          Journal:  Org Chem Int        ISSN: 2090-200X


  17 in total

1.  Construction of quaternary stereocenters: new perspectives through enantioselective Michael reactions.

Authors:  Jens Christoffers; Angelika Baro
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-17       Impact factor: 15.336

2.  Construction of quaternary stereocenters by efficient and practical conjugate additions to alpha,beta-unsaturated ketones with a chiral organic catalyst.

Authors:  Fanghui Wu; Hongming Li; Ran Hong; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-30       Impact factor: 15.336

3.  Asymmetric iminium ion catalysis: an efficient enantioselective synthesis of pyranonaphthoquinones and beta-lapachones.

Authors:  Magnus Rueping; Erli Sugiono; Estíbaliz Merino
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Construction of 5,6-Ring Fused 2-Pyridones: An Effective Annulation Tactic Achieved in Water.

Authors:  Amos B Smith; Onur Atasoylu; Douglas C Beshore
Journal:  Synlett       Date:  2009-01-01       Impact factor: 2.454

5.  Synthesis and antimicrobial activity of some new carbazoles, indazoles, quinolines, quinazolines and naphthalenes from 3-methyl-5-phenyl-6-benzylidene-2-cyclohexene-1-one.

Authors:  F Z El-Ablak; H A Etman; M A Metwally
Journal:  Boll Chim Farm       Date:  1995-02

6.  Enantioselective Michael addition of beta-keto esters to methyl vinyl ketone employing a chiral N,N'-dioxide-scandium trifluoromethanesulfonate complex as a catalyst.

Authors:  M Nakajima; Y Yamaguchi; S Hashimoto
Journal:  Chem Commun (Camb)       Date:  2001-09-07       Impact factor: 6.222

7.  Catalytic asymmetric Michael reaction of beta-keto esters: effects of the linker heteroatom in linked-BINOL.

Authors:  Keisuke Majima; Ryo Takita; Akihiro Okada; Takashi Ohshima; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2003-12-24       Impact factor: 15.419

8.  Aminoacetyl moiety as a potential surrogate for diacylhydrazine group of SC-51089, a potent PGE2 antagonist, and its analogs.

Authors:  E A Hallinan; T J Hagen; S Tsymbalov; R K Husa; A C Lee; A Stapelfeld; M A Savage
Journal:  J Med Chem       Date:  1996-01-19       Impact factor: 7.446

9.  Design and synthesis of novel 2-methyl-4,5-substitutedbenzo[f]-3,3a,4,5-tetrahydro-pyrazolo[1,5-d][1,4]oxazepin-8(7H)-one derivatives as telomerase inhibitors.

Authors:  Xin-Hua Liu; Ying-Ming Jia; Bao-An Song; Zhi-xiang Pang; Song Yang
Journal:  Bioorg Med Chem Lett       Date:  2012-12-03       Impact factor: 2.823

10.  Sordarin oxazepine derivatives as potent antifungal agents.

Authors:  Michael H Serrano-Wu; Denis R St Laurent; Yijun Chen; Stella Huang; Kin-Ray Lam; James A Matson; Charles E Mazzucco; Terry M Stickle; Thomas P Tully; Henry S Wong; Dolatrai M Vyas; Balu N Balasubramanian
Journal:  Bioorg Med Chem Lett       Date:  2002-10-07       Impact factor: 2.823

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