Electro-generated ortho-quinoide intermediates: templates for feasible construction of a series of novel imidazo[2,1-b]thiazole derivatives through one-pot five-step domino hetero-annulation process

Electro-generated ortho-quinoide intermediates: templates for feasible construction of a series... Res Chem Intermed (2015) 41:6185–6197 DOI 10.1007/s11164-014-1731-5 Electro-generated ortho-quinoide intermediates: templates for feasible construction of a series of novel imidazo[2,1-b]thiazole derivatives through one-pot five- step domino hetero-annulation process • • Abdolhamid Alizadeh Mohammad M. Khodaei Tayyebeh Kanjouri Mustaffa Shamsuddin Received: 26 February 2014 / Accepted: 26 May 2014 / Published online: 14 June 2014 Springer Science+Business Media Dordrecht 2014 Abstract A series of novel polycyclic structures, with an imidazothiazole central core, were successfully synthesized through the anodic oxidation of catechols in the presence of 2-imidazolidine thione, as nucleophiles in aqueous solution. The cyclic voltammetric results indicated that one-pot multi-step sequential reactions occur between the electrochemically derived o-benzoquinones intermediates and nucleophiles affording fused polyheterocyclic compounds. The mechanism of these catalyst-free, tandem reactions are proved as ECECE or ECECCE pathways using potentiostatic and galvanostatic coulometries. In addition, the electrosyntheses of fused imidazo[2,1-b]thiazoles have been successfully performed in ambient conditions in an undivided cell using an environmentally friendly method with high atom economy and current efficiency. The novel fused polyheterocycles were fully char- 1 13 acterized by FT-IR, HNMR, C NMR, and HR-MS spectrometric methods. Keywords Quinoide intermediates  Domino reactions  Imidazothiazoles Potentiostatic  Galvanostatic  Heterocycles Electronic supplementary material The http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Electro-generated ortho-quinoide intermediates: templates for feasible construction of a series of novel imidazo[2,1-b]thiazole derivatives through one-pot five-step domino hetero-annulation process

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Publisher
Springer Netherlands
Copyright
Copyright © 2014 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-014-1731-5
Publisher site
See Article on Publisher Site

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