doi: 10.1021/ja1027327.
Copper-catalyzed synthesis of azaspirocyclohexadienones from alpha-azido-N-arylamides under an oxygen atmosphere
Affiliations
- PMID: 20462196
- DOI: 10.1021/ja1027327
Item in Clipboard
Copper-catalyzed synthesis of azaspirocyclohexadienones from alpha-azido-N-arylamides under an oxygen atmosphere
J Am Chem Soc.
.
Abstract
A copper-catalyzed reaction of alpha-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from alpha-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C=O bonds. The preliminary investigation revealed that molecular oxygen is a prerequisite for achieving the present catalytic cyclization and that one of the oxygen atoms of O(2) was found to be incorporated into the cyclohexadienone moiety.
Similar articles
-
Generation of iminyl copper species from alpha-azido carbonyl compounds and their catalytic C-C bond cleavage under an oxygen atmosphere.Org Lett. 2010 May 7;12(9):2052-5. doi: 10.1021/ol100522z. Org Lett. 2010. PMID: 20337491
-
Copper-catalyzed aerobic spirocyclization of biaryl-N-H-imines via 1,4-aminooxygenation of benzene rings.Org Lett. 2012 Jul 6;14(13):3550-3. doi: 10.1021/ol301583y. Epub 2012 Jun 15. Org Lett. 2012. PMID: 22702395
-
Synthesis of spirodienones by intramolecular ipso-cyclization of N-methoxy-(4-halogenophenyl)amides using [hydroxy(tosyloxy)iodo]benzene in trifluoroethanol.J Org Chem. 2003 Jun 27;68(13):5429-32. doi: 10.1021/jo034318w. J Org Chem. 2003. PMID: 12816516
-
Palladium-catalyzed intramolecular amidation of C(sp2)-H bonds: synthesis of 4-aryl-2-quinolinones.J Org Chem. 2010 Jun 4;75(11):3900-3. doi: 10.1021/jo100557s. J Org Chem. 2010. PMID: 20446748
-
Recent advances in copper-catalyzed dehydrogenative functionalization via a single electron transfer (SET) process.Chem Soc Rev. 2012 May 7;41(9):3464-84. doi: 10.1039/c2cs15323h. Epub 2012 Feb 20. Chem Soc Rev. 2012. PMID: 22349590 Review.
Cited by
-
Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines.Beilstein J Org Chem. 2015 Oct 19;11:1933-43. doi: 10.3762/bjoc.11.209. eCollection 2015. Beilstein J Org Chem. 2015. PMID: 26664613 Free PMC article.
-
In situ generation of N-unsubstituted imines from alkyl azides and their applications for imine transfer via copper catalysis.Sci Adv. 2017 Aug 9;3(8):e1700826. doi: 10.1126/sciadv.1700826. eCollection 2017 Aug. Sci Adv. 2017. PMID: 28808683 Free PMC article.
-
Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air.J Am Chem Soc. 2018 Apr 18;140(15):5300-5310. doi: 10.1021/jacs.8b01886. Epub 2018 Apr 9. J Am Chem Soc. 2018. PMID: 29547276 Free PMC article.
-
A dinuclear palladium catalyst for α-hydroxylation of carbonyls with O2.J Am Chem Soc. 2011 Feb 16;133(6):1760-2. doi: 10.1021/ja108396k. Epub 2011 Jan 19. J Am Chem Soc. 2011. PMID: 21247109 Free PMC article.
-
Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides.J Am Chem Soc. 2013 Jan 16;135(2):620-3. doi: 10.1021/ja3113565. Epub 2013 Jan 3. J Am Chem Soc. 2013. PMID: 23265139 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
