Literature DB >> 21985422

Nonconcerted cycloaddition of 2H-azirines to acylketenes: a route to N-bridgehead heterocycles.

Alexander F Khlebnikov1, Mikhail S Novikov, Viktoriia V Pakalnis, Dmitry S Yufit.   

Abstract

Reactions of acylketenes, generated from diazo diketones, with 2-unsubstituted and 2-monosubstituted 3-aryl-2H-azirines lead to 1:1 or 2:1 adducts, which are derivatives of 5-oxa-1-azabicyclo[4.1.0]hept-3-ene or 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene. According to DFT B3LYP/6-31G(d) computations, the formation of (4+2)-monoadducts proceeds via a stepwise non-pericyclic mechanism. Reaction with methanol transforms quantitatively both 1:1 and 2:1 adducts into 1,4-oxazepine derivatives.

Entities:  

Year:  2011        PMID： 21985422     DOI： 10.1021/jo201563b

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  Azirinium ylides from α-diazoketones and 2H-azirines on the route to 2H-1,4-oxazines: three-membered ring opening vs 1,5-cyclization.

Authors:  Nikolai V Rostovskii; Mikhail S Novikov; Alexander F Khlebnikov; Galina L Starova; Margarita S Avdontseva
Journal:  Beilstein J Org Chem       Date:  2015-03-02       Impact factor: 2.883

2.  [3 + 2]-Cycloadditions of nitrile ylides after photoactivion of vinyl azides under flow conditions.

Authors:  Stephan Cludius-Brandt; Lukas Kupracz; Andreas Kirschning
Journal:  Beilstein J Org Chem       Date:  2013-08-26       Impact factor: 2.883

3.  Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems.

Authors:  Alexander F Khlebnikov; Mikhail S Novikov; Viktoriia V Pakalnis; Roman O Iakovenko; Dmitry S Yufit
Journal:  Beilstein J Org Chem       Date:  2014-04-04       Impact factor: 2.883
  3 in total

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