Literature DB >> 27272954

Synthesis of isoindolin-1-one derivatives via multicomponent reactions of methyl 2-formylbenzoate and intramolecular amidation.

Jie Lei1,2,3, Zhi-Gang Xu4, Shi-Qiang Li3, Jia Xu3, Jin Zhu2,3, Zhong-Zhu Chen5.   

Abstract

Four series of heterocyclic compounds were obtained using Ugi-type multicomponent reactions (MCRs) with methyl 2-formylbenzoate as one of the starting materials. A facile and efficient one-pot procedure was suitable for all the MCRs under acidic conditions. This process provided access to four series of complex and potentially biologically active scaffolds.

Entities:  

Keywords:  Cyclization; Heterocycles; Intramolecular amidation; MCRs; One-pot procedure; UDC strategy; Ugi-type multicomponent reactions

Mesh:

Substances:

Year:  2016        PMID: 27272954     DOI: 10.1007/s11030-016-9679-6

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


  22 in total

1.  Unique Structures Generated by Ugi 3CC Reactions Using Bifunctional Starting Materials Containing Aldehyde and Carboxylic Acid.

Authors:  Jundong Zhang; Alan Jacobson; James R. Rusche; Walter Herlihy
Journal:  J Org Chem       Date:  1999-02-05       Impact factor: 4.354

2.  Rapid synthesis of highly functionalised α-amino amides and medium ring lactones using multicomponent reactions of amino alcohols and isocyanides.

Authors:  Martin Bachman; Sam E Mann; Tom D Sheppard
Journal:  Org Biomol Chem       Date:  2011-11-10       Impact factor: 3.876

Review 3.  "Multi-component reactions : emerging chemistry in drug discovery" 'from xylocain to crixivan'.

Authors:  Christopher Hulme; Vijay Gore
Journal:  Curr Med Chem       Date:  2003-01       Impact factor: 4.530

4.  General one-pot, two-step protocol accessing a range of novel polycyclic heterocycles with high skeletal diversity.

Authors:  Zhigang Xu; Muhammad Ayaz; Alexandra A Cappelli; Christopher Hulme
Journal:  ACS Comb Sci       Date:  2012-07-12       Impact factor: 3.784

5.  Rapid two-step synthesis of benzimidazo[1',2':1,5]pyrrolo[2,3-c]isoquinolines by a three-component coupling reaction.

Authors:  Bharat D Narhe; Min-Huan Tsai; Chung-Ming Sun
Journal:  ACS Comb Sci       Date:  2014-06-20       Impact factor: 3.784

6.  Facile, novel two-step syntheses of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines.

Authors:  Zhigang Xu; Arthur Y Shaw; Justin Dietrich; Alexandra P Cappelli; Gary Nichol; Christopher Hulme
Journal:  Mol Divers       Date:  2012-01-12       Impact factor: 2.943

7.  Efficient assembly of iminodicarboxamides by a "truly" four-component reaction.

Authors:  Kareem Khoury; Mantosh K Sinha; Tadamichi Nagashima; Eberhardt Herdtweck; Alexander Dömling
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-11       Impact factor: 15.336

8.  Various cyclization scaffolds by a truly Ugi 4-CR.

Authors:  Mantosh K Sinha; Kareem Khoury; Eberhardt Herdtweck; Alexander Dömling
Journal:  Org Biomol Chem       Date:  2013-06-13       Impact factor: 3.876

9.  Multicomponent assembly of diverse pyrazin-2(1H)-one chemotypes.

Authors:  Jhonny Azuaje; Abdelaziz El Maatougui; José M Pérez-Rubio; Alberto Coelho; Franco Fernández; Eddy Sotelo
Journal:  J Org Chem       Date:  2013-04-12       Impact factor: 4.354

10.  Passerini reaction--amine deprotection--acyl migration (PADAM): A convenient strategy for the solid-phase preparation of peptidomimetic compounds.

Authors:  Luca Banfi; Andrea Basso; Giuseppe Guanti; Renata Riva
Journal:  Mol Divers       Date:  2003       Impact factor: 2.943

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