Literature DB >> 26703123

One-pot tandem Ugi-4CR/S(N)Ar approach to highly functionalized quino[2,3-b][1,5]benzoxazepines.

Mehdi Ghandi1, Nahid Zarezadeh2, Alireza Abbasi2.   

Abstract

We have developed a convenient and facile method for the synthesis of functionalized diverse quino[2,3-b][1,5]benzoxazepines. These new compounds were synthesized through a one-pot sequential Ugi-4CR/base-free intramolecular aromatic nucleophilic substitution (S(N)Ar) reaction in moderate to good yields from readily available starting materials. Structural confirmation of the products is confirmed by analytical data and X-ray crystallography.

Entities:  

Keywords:  2-Chloroquinoline-3-carbaldehyde; MCRs; Quino[2, 3-b][1, 5]benzoxazepine; Ugi reaction; reaction

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Substances：

Year:  2015        PMID： 26703123     DOI： 10.1007/s11030-015-9651-x

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


  21 in total

1.  Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis.

Authors:  Annamaria Lilienkampf; Jialin Mao; Baojie Wan; Yuehong Wang; Scott G Franzblau; Alan P Kozikowski
Journal:  J Med Chem       Date:  2009-04-09       Impact factor: 7.446

2.  Tricyclic azepine derivatives: pyrimido[4,5-b]-1,4-benzoxazepines as a novel class of epidermal growth factor receptor kinase inhibitors.

Authors:  Leon Smith; Evgueni L Piatnitski; Alexander S Kiselyov; Xiaohu Ouyang; Xiaoling Chen; Sabina Burdzovic-Wizemann; Yongjiang Xu; Weitao Pan; Xin Chen; Ying Wang; Robin L Rosler; Sheetal N Patel; Hui-Hsien Chiang; Daniel L Milligan; John Columbus; Wai C Wong; Jacqueline F Doody; Yaron R Hadari
Journal:  Bioorg Med Chem Lett       Date:  2006-01-18       Impact factor: 2.823

3.  Synthesis and enantioselective hydrogenation of seven-membered cyclic imines: substituted dibenzo[b,f][1,4]oxazepines.

Authors:  Kai Gao; Chang-Bin Yu; Wei Li; Yong-Gui Zhou; Xumu Zhang
Journal:  Chem Commun (Camb)       Date:  2011-05-31       Impact factor: 6.222

4.  One-pot synthesis of spiropyrroloquinoline-isoindolinone and their aza-analogs via the Ugi-4CR/metal-free intramolecular bis-annulation process.

Authors:  Mehdi Ghandi; Nahid Zarezadeh; Alireza Abbasi
Journal:  Org Biomol Chem       Date:  2015-08-14       Impact factor: 3.876

5.  Asymmetric alkynylation of seven-membered cyclic imines by combining chiral phosphoric acids and Ag(I) catalysts: synthesis of 11-substituted-10,11-dihydrodibenzo[b,f][1,4]oxazepine derivatives.

Authors:  Yuan-Yuan Ren; You-Qing Wang; Shuang Liu
Journal:  J Org Chem       Date:  2014-11-14       Impact factor: 4.354

6.  Preparation of substituted pyrimido[4,5-b]-1,4-benzoxazepines, thiazepines, and diazepines via a Pictet-Spengler cyclization.

Authors:  Matthew A J Duncton; Leon M Smith; Sabina Burdzovic-Wizeman; Aaron Burns; Hu Liu; Yunyu Mao; Wai C Wong; Alexander S Kiselyov
Journal:  J Org Chem       Date:  2005-11-11       Impact factor: 4.354

7.  Dibenzoxazepinium ylides: facile access and 1,3-dipolar cycloaddition reactions.

Authors:  Alexander F Khlebnikov; Mikhail S Novikov; Petr P Petrovskii; Joerg Magull; Arne Ringe
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

8.  Synthesis and antitumoral activity of novel thiazolobenzotriazole, thiazoloindolo[3,2-c]quinoline and quinolinoquinoline derivatives.

Authors:  Anne Beauchard; Alexis Jaunet; Laurence Murillo; Brigitte Baldeyrou; Amélie Lansiaux; Jean-René Chérouvrier; Lisianne Domon; Laurent Picot; Christian Bailly; Thierry Besson; Valérie Thiéry
Journal:  Eur J Med Chem       Date:  2009-04-14       Impact factor: 6.514

9.  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

10.  New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine.

Authors:  G Walther; H Daniel; W D Bechtel; K Brandt
Journal:  Arzneimittelforschung       Date:  1990-04
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  3 in total

1.  One-pot synthesis of novel 1-(1H-tetrazol-5-yl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives via an Ugi-azide 4CR process.

Authors:  Mehdi Ghandi; Saleh Salahi; Abuzar Taheri; Alireza Abbasi
Journal:  Mol Divers       Date:  2017-12-11       Impact factor: 2.943

2.  The regioselective one-pot four-component synthesis of novel functionalized 4H-pyrano[2, 3-b]quinoline derivatives using DABCO as a homogeneous organocatalyst.

Authors:  Masumeh Heydari; Ali Asghar Mohammadi; Mohammadreza Mosleh
Journal:  Mol Divers       Date:  2022-09-07       Impact factor: 3.364

Review 3.  Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs.

Authors:  Wafaa S Hamama; Mona E Ibrahim; Ayaa A Gooda; Hanafi H Zoorob
Journal:  RSC Adv       Date:  2018-02-23       Impact factor: 4.036
  3 in total

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