Literature DB >> 11594818

A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-Knorr sequence.

R U Braun1, K Zeitler, T J Müller.   

Abstract

[reaction: see text]. 1,2,3,5-tetrasubstituted pyrroles can be synthesized in good yields in a one-pot, three-step, four-component process by a coupling-isomerization-Stetter reaction-Paal-Knorr sequence of an electron-poor (hetero)aryl halide, a terminal propargyl alcohol, an aldehyde, and a primary amine. The structures of the 1,4-diketone 4f and the pyrrole 6b were additionally supported by X-ray structure analyses.

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Year:  2001        PMID: 11594818     DOI: 10.1021/ol0165185

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  12 in total

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Review 2.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

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Authors:  Benjamin C Milgram; Katrine Eskildsen; Steven M Richter; W Robert Scheidt; Karl A Scheidt
Journal:  J Org Chem       Date:  2007-04-14       Impact factor: 4.354

4.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

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5.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
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6.  Coupling-isomerization-coupling sequences switched on by propargyl alcohol-enone-isomerization.

Authors:  Roland U Braun; Thomas J J Müller
Journal:  Mol Divers       Date:  2003       Impact factor: 2.943

7.  Vinylogous reactivity of enol diazoacetates with donor-acceptor substituted hydrazones. Synthesis of substituted pyrazole derivatives.

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8.  Ribose conversion with amino acids into pyrraline platform chemicals - expeditious synthesis of diverse pyrrole-fused alkaloid compounds.

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9.  Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones.

Authors:  Murat Kucukdisli; Dorota Ferenc; Marcel Heinz; Christine Wiebe; Till Opatz
Journal:  Beilstein J Org Chem       Date:  2014-02-24       Impact factor: 2.883

10.  One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines.

Authors:  Christian Muschelknautz; Robin Visse; Jan Nordmann; Thomas J J Müller
Journal:  Beilstein J Org Chem       Date:  2014-03-05       Impact factor: 2.883

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