+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Synthesis of 1-Azaanthraquinone: Sequential C-N Bond Formation/Lewis Acid Catalyzed Intramolecular Cyclization Strategy

Synthesis of 1-Azaanthraquinone: Sequential C-N Bond Formation/Lewis Acid Catalyzed Intramolecular Cyclization Strategy

Journal of Organic Chemistry 82(15): 8309-8316

A synthetic strategy has been developed for the synthesis of 1-azaanthraquinones. This synthetic protocol consists of sequential Pd-catalyzed carbon-nitrogen bond formation followed by Lewis acid catalyzed intramolecular cyclization. The Pd-catalyzed aminated intermediate was isolated and characterized. This sequential reactions strategy provides a wide range of 1-azaanthraquinones with good yields.

Please choose payment method:

(PDF emailed within 0-6 h: $19.90)

Accession: 060308253

Download citation: RISBibTeXText

PMID: 28677967

DOI: 10.1021/acs.joc.7b01427

Related references

An enantioselective strategy for the total synthesis of (S)-tylophorine via catalytic asymmetric allylation and a one-pot DMAP-promoted isocyanate formation/Lewis acid catalyzed cyclization sequence. Organic & Biomolecular Chemistry 12(22): 3616-3621, 2015

Synthesis of Substituted Benzo[b]thiophenes via Sequential One-Pot, Copper-Catalyzed Intermolecular C-S Bond Formation and Palladium-Catalyzed Intramolecular Arene-Alkene Coupling of Bis(het)aryl/alkyl-1,3-monothiodiketones and o-Bromoiodoarenes. Organic Letters 19(7): 1512-1515, 2017

Phosphazene base-catalyzed intramolecular cyclization for efficient synthesis of benzofurans via carbon-carbon bond formation. Chemical Communications: 5248-5250, 2009

Heterocycle formation via palladium-catalyzed intramolecular oxidative C-H bond functionalization: an efficient strategy for the synthesis of 2-aminobenzothiazoles. Organic Letters 11(13): 2792-2795, 2009

Copper-catalyzed intramolecular N-S bond formation by oxidative dehydrogenative cyclization. Journal of Organic Chemistry 78(14): 7337-7342, 2013

Lewis Acid Catalyzed Cyclization Reactions of Ethenetricarboxylates via Intramolecular Hydride Transfer. Journal of Organic Chemistry 82(13): 6748-6763, 2017

One-pot synthesis of 4-methylisoquinolines via a sequential Pd-catalyzed Heck reaction and intramolecular cyclization. Organic & Biomolecular Chemistry 11(42): 7262-7266, 2014

Intramolecular lewis acid catalyzed heterocycloaddition reactions cyclization of ketone heterodienophiles in the dihydrotropone series. Tetrahedron Letters 27(29): 3329-3332, 1986

Rh(III)-catalyzed addition of alkenyl C-H bond to isocyanates and intramolecular cyclization: direct synthesis 5-ylidenepyrrol-2(5H)-ones. Organic Letters 15(8): 1814-1817, 2013

Palladium catalyzed N-H bond insertion and intramolecular cyclization cascade: the divergent synthesis of heterocyclics. Organic & Biomolecular Chemistry 12(16): 2533-2537, 2014

Room temperature intramolecular hydro-O-alkylation of aldehydes: sp3 C-H functionalization via a Lewis acid catalyzed tandem 1,5-hydride transfer/cyclization. Organic Letters 7(24): 5429-5431, 2005

Determining the scope of the organolanthanide-catalyzed, sequential intramolecular amination/cyclization reaction: formation of substituted quinolizidines, indolizidines, and pyrrolizidines. Journal of Organic Chemistry 68(24): 9214-9220, 2003

A reaction for sp(3)-sp(3) C-C bond formation via cooperation of Lewis acid-promoted/Rh-catalyzed C-H bond activation. Journal of the American Chemical Society 127(31): 10836-7, 2005

Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions. Journal of the American Chemical Society 137(45): 14341-8, 2016

Ready synthesis of free N-H 2-arylindoles via the copper-catalyzed amination of 2-bromo-arylacetylenes with aqueous ammonia and sequential intramolecular cyclization. Organic & Biomolecular Chemistry 9(13): 4983-4986, 2011