RSS-Feed abonnieren
DOI: 10.1055/s-0030-1259507
Novel Palladium-Free Synthesis of a Key Quinazolinap Precursor
Publikationsverlauf
Publikationsdatum:
25. Januar 2011 (online)
![](https://www.thieme-connect.de/media/synlett/201103/lookinside/thumbnails/10.1055-s-0030-1259507-1.jpg)
Abstract
A novel, short synthetic route has been successfully developed for a key precursor of Quinazolinap ligands. The key step is a Friedel-Crafts-type reaction between 2-naphthol and 4-chloroquinazoline, with moderate to quantitative yields recorded. A variation of this reaction allows for the introduction of an amine group on the naphthalene unit.
Key words
arylation - Lewis acids - ligands - quinazolines - phenols
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Jacobsen EN.Pfaltz A.Yamamoto H. Comprehensive Asymmetric Catalysis Vol. 1: Springer; Berlin: 1999. -
1b
Jacobsen EN.Pfaltz A.Yamamoto H. Comprehensive Asymmetric Catalysis Vol. 2: Springer; Berlin: 1999. -
1c
Jacobsen EN.Pfaltz A.Yamamoto H. Comprehensive Asymmetric Catalysis Vol. 3: Springer; Berlin: 1999. -
2a
McCarthy M.Guiry PJ. Tetrahedron 2001, 57: 3809 -
2b
Guiry PJ.McCarthy M.Lacey PM.Saunders CP.Kelly S.Connolly DJ. Curr. Org. Chem. 2000, 4: 835 -
2c
Saunders CP.Guiry PJ. Adv. Synth. Catal. 2004, 346: 497 -
2d
Li Y.-M.Kwong F.-Y.Yu W.-Y.Chan ASC. Coord. Chem. Rev. 2007, 251: 2119 -
3a
Alock NW.Brown JM.Hulmes DI. Tetrahedron: Asymmetry 1993, 4: 743 -
3b
Brown JM.Hulmes DI.Guiry PJ. Tetrahedron 1994, 50: 4493 - 4
Doucet H.Fernandez E.Layzell TP.Brown JM. Chem. Eur. J. 1999, 5: 1320 - 5
Gommermann N.Koradin C.Polborn K.Knochel P. Angew. Chem. Int. Ed. 2003, 42: 5763 - 6
Morgan JB.Miler SP.Morken JP. J. Am. Chem. Soc. 2003, 125: 8702 - 7
Chen C.Li X.Schreiber SL. J. Am. Chem. Soc. 2003, 125: 10174 -
8a
McCarthy M.Goddard R.Guiry PJ. Tetrahedron: Asymmetry 1999, 10: 2797 -
8b
Lacey PM.McDonnell C.Guiry PJ. Tetrahedron Lett. 2000, 41: 2457 -
8c
Connolly DJ.Lacey PM.McCarthy M.Saunders CP.Carroll AM.Goddard R.Guiry PJ. J. Org. Chem. 2004, 69: 6572 -
8d
Flanagan SP.Goddard R.Guiry PJ. Tetrahedron 2005, 61: 9808 -
8e
Fekner T.Müller-Bunz H.Guiry PJ. Org. Lett. 2006, 8: 5109 -
8f
Maxwell AC.Franc C.Pouchain L.Müller-Bunz H.Guiry PJ. Org. Biomol. Chem. 2008, 6: 3848 -
8g
Fekner T.Müller-Bunz H.Guiry PJ. Eur. J. Org. Chem. 2008, 5055 -
8h
McCarthy M.Hooper MW.Guiry PJ. Chem. Commun. 2000, 1333 -
8i
Maxwell AC.Flanagan SP.Goddard R.Guiry PJ. Tetrahedron: Asymmetry 2010, 21: 1458 -
8j
Fleming WJ.Muller-Bunz H.Guiry PJ. Eur. J. Org. Chem. 2010, 5996 - 9
Pal M.Batchu VR.Parasuraman K.Yeleswarapu KR. J. Org. Chem. 2003, 68: 6806 -
10a
Knopfel TF.Aschwanden P.Ichikawa T.Watanabe T.Carreira EM. Angew. Chem. Int. Ed. 2004, 43: 5971 -
10b
Knopfel TF.Zarotti P.Ichikawa T.Carreira EM. J. Am. Chem. Soc. 2005, 127: 9682 -
10c
Carreira EM. inventors; US Patent, 20050277772 . , - 11
Hentrich W,Hardtmann M, andKnoche R. inventors; US Patent, 1780879. - 12
Kumar S.Sahu DP. J. Heterocycl. Chem. 2009, 46: 748 -
13a
Mintas M.Mihaljevic V. J. Chem. Soc., Perkin Trans. 2 1990, 619 -
13b
Harmange J.-C.Weiss MM.Germain J.Polverino AJ.Borg G.Bready J.Chen D.Choquette D.Coxon A.DeMelfi T.DiPietro L.Doerr N.Estrada J.Flynn J.Graceffa RF.Harriman SP.Kaufman S.La DS.Long A.Martin MW.Neervannan S.Patel VF.Potashman M.Regal K.Roveto PM.Schrag ML.Starnes C.Tasker A.Teffera Y.Wang L.White RD.Whittington DA.Zanon R. J. Med. Chem. 2008, 51: 1649 -
13c
Hennequin LFA. inventors; US Patent 20080058342. - 14
Beugelmans R.Bois-Choussy M. J. Org. Chem. 1991, 56: 2518
References and Notes
Typical Procedure: 2-Naphthol (1 mmol), 4-chloroquinaz-oline (1 mmol) and AlCl3 (3 mmol) were suspended in DCE (3 mL) in a Schlenk tube under a nitrogen atmosphere. The mixture was heated at 80 ˚C for 3.5 h and then diluted with CH2Cl2 (15 mL). The mixture was washed with 1 M NaOH solution (15 mL), sat. NH4Cl solution (15 mL), H2O (15 mL), brine (15 mL), dried over MgSO4, filtered and eva-porated under reduced pressure. The crude product could be directly used in the subsequent steps of the synthesis without significant loss of yield compared to the use of pure compound. Nevertheless, purification was achievable by column chromatography using silica gel and CH2Cl2 as eluent. Compounds were identical to known samples.