Literature DB >> 26537729

Ethyl 3-(2,4-dioxocyclohexyl)propanoate as a novel precursor for N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones and their corresponding 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and 7-hydroxyquinolin-2(1H)-ones synthesis.

Vandna Thakur1,2, Dharminder Sharma1, Pralay Das3,4.   

Abstract

Ethyl 3-(2,4-dioxocyclohexyl)propanoate has been explored as a precursor for the synthesis of N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones following conventional protecvtion, selective amidation, and deprotective-cyclization approaches. Moreover, a facile process for the selective dehydrogenative aromatization of these diones was developed to afford the corresponding N-substituted 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and N-substituted 7-hydroxyquinolin-2(1H)-ones under mild conditions.

Entities:  

Keywords:  7-Hydroxy-quinlin-2(1H)-one; Cyclohexane-1, 3-dione; Dehydrogenative aromatization; Heterocycles; Microwave irradiation; Tetrahydroquinoline-2,7-dione

Mesh:

Substances:

Year:  2015        PMID: 26537729     DOI: 10.1007/s11030-015-9643-x

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  16 in total

Review 1.  Quinoline, quinazoline and acridone alkaloids.

Authors:  J P Michael
Journal:  Nat Prod Rep       Date:  2001-10       Impact factor: 13.423

2.  Inhibition of autoimmune disease by the immunomodulator linomide correlates with the ability to activate macrophages.

Authors:  E Dahlén; M Andersson; K Dawe; A C Tellander; C Brunmark; A Björk; G Hedlund
Journal:  Autoimmunity       Date:  2000-10       Impact factor: 2.815

3.  Sodium methoxide: a simple but highly efficient catalyst for the direct amidation of esters.

Authors:  Takashi Ohshima; Yukiko Hayashi; Kazushi Agura; Yuka Fujii; Asako Yoshiyama; Kazushi Mashima
Journal:  Chem Commun (Camb)       Date:  2012-04-27       Impact factor: 6.222

4.  Quinolone antibacterial agents. Synthesis and structure-activity relationships of 8-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids.

Authors:  J P Sanchez; J M Domagala; S E Hagen; C L Heifetz; M P Hutt; J B Nichols; A K Trehan
Journal:  J Med Chem       Date:  1988-05       Impact factor: 7.446

5.  New potential biologically active compounds: design and an efficient synthesis of N-substituted 4-aryl-4,6,7,8-tetrahydroquinoline-2,5(1H,3H)-diones under microwave irradiation.

Authors:  Shujiang Tu; Xiaotong Zhu; Jinpeng Zhang; Jianing Xu; Yan Zhang; Qian Wang; Runhong Jia; Bo Jiang; Junyong Zhang; Changsheng Yao
Journal:  Bioorg Med Chem Lett       Date:  2006-03-24       Impact factor: 2.823

6.  Novel antipsychotic agents with dopamine autoreceptor agonist properties: synthesis and pharmacology of 7-[4-(4-phenyl-1-piperazinyl)butoxy]-3,4-dihydro-2(1H)-quinolinone derivatives.

Authors:  Y Oshiro; S Sato; N Kurahashi; T Tanaka; T Kikuchi; K Tottori; Y Uwahodo; T Nishi
Journal:  J Med Chem       Date:  1998-02-26       Impact factor: 7.446

7.  Synthesis of 2-quinolones via palladium-catalyzed carbonylative annulation of internal alkynes by N-substituted o-iodoanilines.

Authors:  Dmitry V Kadnikov; Richard C Larock
Journal:  J Org Chem       Date:  2004-10-01       Impact factor: 4.354

8.  Efficient preparation of 4-hydroxyquinolin-2(1H)-one derivatives with silver-catalyzed carbon dioxide incorporation and intramolecular rearrangement.

Authors:  Tomonobu Ishida; Satoshi Kikuchi; Tohru Yamada
Journal:  Org Lett       Date:  2013-07-02       Impact factor: 6.005

9.  Selective dual inhibitors of CYP19 and CYP11B2: targeting cardiovascular diseases hiding in the shadow of breast cancer.

Authors:  Qingzhong Hu; Lina Yin; Rolf W Hartmann
Journal:  J Med Chem       Date:  2012-08-03       Impact factor: 7.446

Review 10.  Recent syntheses of 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1H)-quinolinones using domino reactions.

Authors:  Baskar Nammalwar; Richard A Bunce
Journal:  Molecules       Date:  2013-12-24       Impact factor: 4.411

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