High-yielding synthesis of Nefopam analogues (functionalized benzoxazocines) by sequential one-pot cascade operations

Dhevalapally B. Ramachary; Vidadala V. Narayana; M. Shiva Prasad; Kinthada Ramakumar

doi:10.1039/B910397J

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Organic & Biomolecular Chemistry

Issue 17, 2009

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High-yielding synthesis of Nefopam analogues (functionalized benzoxazocines) by sequential one-pot cascade operations

Dhevalapally B. Ramachary , Vidadala V. Narayana , M. Shiva Prasad and Kinthada Ramakumar

Org. Biomol. Chem., 2009, 7, 3372-3378

DOI: 10.1039/B910397J
Received 27 May 2009, Accepted 23 Jun 2009
First published on the web 03 Jul 2009

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Abstract
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An efficient amine-/ruthenium-catalyzed three-step process for the synthesis of Nefopam analogues was achieved through combinations of cascade enamine amination/iso-aromatization/allylation and diene or enyne metathesis as key steps starting from functionalized Hagemann's esters. In this communication, we discovered the application of ruthenium-catalysis on olefins containing free amines without in situ formation of salts.

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Experimental procedures and analytical data (¹H NMR, ¹³C NMR and HRMS) for all new compounds
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Organic & Biomolecular Chemistry

High-yielding synthesis of Nefopam analogues (functionalized benzoxazocines) by sequential one-pot cascade operations

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