Literature DB >> 18553971

Electrophile-induced dearomatizing spirocyclization of N-arylisonicotinamides: a route to spirocyclic piperidines.

Gareth Arnott1, Heloise Brice, Jonathan Clayden, Emma Blaney.   

Abstract

Treatment of N-arylisonicotinamides with trifluoromethanesulfonic anhydride triggers intramolecular nucleophilic attack of the aryl ring on the 4-position of the pyridinium intermediate. The products are spirocyclic dihydropyridines which can be converted to valuable spirocyclic piperidines related to biologically active molecules such as MK-677.

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Year:  2008        PMID: 18553971     DOI: 10.1021/ol801092s

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


  4 in total

Review 1.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

2.  Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones.

Authors:  Heloise Brice; Jonathan Clayden; Stuart D Hamilton
Journal:  Beilstein J Org Chem       Date:  2010-03-02       Impact factor: 2.883

3.  Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant.

Authors:  Mamoru Tobisu; Toshifumi Morioka; Akimichi Ohtsuki; Naoto Chatani
Journal:  Chem Sci       Date:  2015-03-27       Impact factor: 9.825

4.  Direct cyclopropanation of activated N-heteroarenes via site- and stereoselective dearomative reactions.

Authors:  Jiyoun Lee; Donguk Ko; Hyunju Park; Eun Jeong Yoo
Journal:  Chem Sci       Date:  2020-01-10       Impact factor: 9.825

  4 in total

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