Subscribe to RSS
DOI: 10.1055/s-0028-1088074
Microwave-Promoted Solid-Acid-Catalyzed One-Pot Synthesis of Phthalazinones
Publication History
Publication Date:
27 April 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200911/lookinside/thumbnails/10.1055-s-0028-1088074-1.jpg)
Abstract
A one-pot, solid-acid-catalyzed, microwave-assisted synthesis of phthalazinones is described. The commercially available montmorillonite K-10 effectively catalyzed the condensation and substitution reactions. The approach was based on the direct cyclization of phthalaldehydic acid and opianic acid with substituted hydrazines. The reactions provided excellent yields and high selectivities in very short time (5-35 minutes).
Key words
phthalazinones - phthalaldehydic acid - opianic acid - hydrazines - montmorillonite K-10 - microwave heating
-
1a
Gilchrist TL. Heterocyclic Chemistry 3rd ed.: Longman; NJ: 1997. -
1b
Török M.Jakab G.Bérczi A.Dux L.Horváth LI. Biochim. Biophys. Acta 1997, 1326: 193 -
1c
Horváth LI.Török M.Hideg K.Dux L. J. Mol. Recog. 1997, 10: 188 -
1d
Gilchrist TA. J. Chem. Soc., Perkin Trans. 1 1998, 615 -
1e
Nobuyoshi A.Akihiko O.Chikara M.Tatsuya T.Masami O.Hiromitsu S. J. Med. Chem. 1999, 42: 2946 -
1f
Kohling P.Schmidt AM.Eilbracht P. Org. Lett. 2003, 5: 3213 -
1g
Caron S.Vazquez E. J. Org. Chem. 2003, 68: 4104 -
1h
Bringmann G.Tasler S.Endress H.Muhlbacher J. Chem. Commun. 2001, 761 -
1i
Baran PS.Richter JM.Lin DW. Angew. Chem. Int. Ed. 2005, 44: 609 -
1j
Török B.Abid M.London G.Esquibel J.Török M.Mhadgut SC.Yan P.Prakash GKS. Angew. Chem. Int. Ed. 2005, 44: 3086 -
1k
Török M.Abid M.Mhadgut SC.Török B. Biochemistry 2006, 45: 5377 -
2a
Nakajima M.Ohyama K.Nakamura S.Shimada N.Yamazaki H.Yokoi T. Drug Metab. Dispos. 1999, 27: 792 -
2b
NYASC Allergy & Sinus Centers.
http://www.nyallergy.com/medications.php?sid=astelin (May 27, 2007). -
2c
Ukita T.Sugahara M.Terakawa Y.Kuroda T.Wada K.Nakata A.Ohmachi Y.Kikkawa H.Ikezawa K.Naito K. J. Med. Chem. 1999, 42: 1088 - 3
Madhavan GR.Chakrabarti R.Kumar SKB.Misra P.Mamidi RNVS.Balraju V.Kasiram K.Babu RK.Suresh J.Lohray BB.Lohray VB.Iqbal J.Rajagopalan R. Eur. J. Med. Chem. 2001, 36: 627 - 4
El Ashry ESH.Abdel-Rahman AAH.Rashed N.Rasheed HA. Pharmazie 1999, 54: 893 -
6
García-Cadenas, A. E.; del Olmoa, E. L.; López, J.; Ferro, A.; Authib, K.; San Feliciano, A. Abstracts of Papers, Joint Meeting on Medicinal Chemistry, Vienna, Austria, June 20-23, 2005; PO-80.
-
5b
Demirayak S.Karaburun AC.Beis R. Eur. J. Med. Chem. 2004, 39: 1089 - 7
Engel J,Kutscher B,Fleischhauer I,Szelenyi S,Metzenauer P, andWerner U. inventors; Eur. Patent EP 590551. ; Chem. Abstr. 1994, 121, 50100 -
8a
Kornet MJ.Shackleford G. J. Heterocycl. Chem. 1999, 36: 1095 -
8b
Huang YR.Katzenellenbogen JA. Org. Lett. 2000, 2: 2833 - 9
Kassem EM.Kamel MM. Pharmazie 1990, 45: 215 - 10
Cockcroft X.Dillon KJ.Dixon L.Drzewiecki J.Kerrigan F.Loh VM.Martin NMB.Menear KA.Smith GCM. Bioorg. Med. Chem. Lett. 2006, 16: 1040 - 11
McTavish D.Sorkin EM. Drugs 1989, 38: 778 - 12
Van der Mey M.Bommele KM.Boss H.Hatzelmann A.Van Slingerland M.Sterk GJ.Timmerman H. J. Med. Chem. 2003, 46: 2008 -
13a
Sato H,Horie S,Sekikawa N, andOno H. inventors; DE Patent 2,632,656. ; Chem. Abstr. 1977, 86, 171487 -
13b
Hirayama T, andKamada M. inventors; JP Patent 52,027,785. ; Chem. Abstr. 1977, 87, 184540 -
14a
Biniecki S, andMoll M. inventors; PL Patent 60,625, August 5. ; Chem. Abstr. 1971, 74, 76435 -
14b
Raoul P. inventors; DE Patent 2,045,111. ; Chem. Abstr. 1971, 74, 141839 -
15a
Butula I.Ruzdija A.Kalmar J. Croat. Chem. Acta 1979, 52: 43 -
15b
Matsushiro K, andMiyashita M. inventors; JP Patent 49,051,287. ; Chem Abstr. 1974, 81, 169555 - 16
Sutherland JB.Freeman JP.Williams AJ. Appl. Microbiol. Biotechnol. 1998, 49: 445 -
17a
Abid M.Landge SM.Török B. Org. Prep. Proced. Int. 2006, 38: 495 -
17b
Abid M.Spaeth A.Török B. Adv. Synth. Catal. 2006, 348: 2191 -
17c
Abid M.Savolainen M.Landge SM.Hu J.Prakash GKS.Olah GA.Török B. J. Fluorine Chem. 2007, 128: 587 -
17d
Abid M.De Paolis O.Török B. Synlett 2008, 410 - 18
Landge SM.Atanassova V.Thimmaiah M.Török B. Tetrahedron Lett. 2007, 48: 5161 -
19a
Landge SM.Berryman M.Török B. Tetrahedron Lett. 2008, 49: 4505 -
19b
Landge SM.Török B. Catal. Lett. 2008, 122: 338 - 20
Landge SM.Borkin D.Török B. Tetrahedron Lett. 2007, 48: 6372 -
21a
Landge SM.Schmidt A.Outerbridge V.Török B. Synlett 2007, 1600 -
21b
De Paolis O.Baffoe J.Landge SM.Török B. Synthesis 2008, 3423 -
22a
Balogh M.Laszlo P. Organic Chemistry Using Clays Springer-Verlag; Berlin/Heidelberg: 1993. -
22b
Varma RS.Dahiya R.Kumar S. Tetrahedron Lett. 1997, 38: 2039 -
22c
Kappe CO.Stadler A. Microwaves in Organic and Medicinal Chemistry Wiley-VCH; Weinheim: 2005. -
22d
Li A.Li T.Ding T. Chem. Commun. 1997, 1389 -
22e
Dasgupta S.Török B. Org. Prep. Proced. Int. 2008, 40: 1 -
22f
Polshettiwar V.Varma RS. Acc. Chem. Res. 2008, 41: 629 -
22g
Dasgupta S.Török B. Curr. Org. Synth. 2008, 5: 321 -
23a
Jain AC.Khanna VK.Sarpal PD.Seshadri TR. Tetrahedron 1968, 24: 3237 -
23b
Falck JR.Manna S. Tetrahedron Lett. 1981, 22: 619 -
23c
Somogyi L. Liebigs Ann. Chem. 1985, 1679 -
23d
Krasnov KA.Kartsev VG.Santarovich EE. Chem. Heterocycl. Compd. (Engl. Transl.) 2002, 38: 702