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DOI: 10.1055/s-0030-1260312
Palladium-Catalyzed One-Pot Synthesis of Pyrrole-Annulated Coumarin, Quinolone, and 7-Aza-indole Derivatives
Publication History
Publication Date:
13 September 2011 (online)
Abstract
An efficient one-pot approach for the synthesis of highly substituted pyrrolocoumarin, quinolone, and pyrrolopyridine derivatives has been achieved by palladium acetate catalyzed reaction in DMF through initially formed enamine from cyclic and acyclic ketones and 6-amino-5-bromocoumarin, 6-amino-5-bromo-1-methyl quinolone, and 2-amino-3,5-dibromopyridine, respectively.
Key words
pyrrolocoumarin - pyrroloquinolone - pyrrolopyridine - palladium acetate
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Boyd DR.Sharma ND.Barr SA.Carroll JG.Mackerracher D.Malone JF. J. Chem. Soc., Perkin Trans. 1 2000, 3397 -
1b
Bar G.Parsons AF.Thomas CB. Tetrahedron 2001, 57: 4719 -
1c
Lee YR.Kim BS.Kweon HI. Tetrahedron 2000, 56: 3867 -
1d
Pirrung MC.Blume F. J. Org. Chem. 1999, 64: 36-42 -
1e
Dickinson JM. Nat. Prod. Rep. 1993, 10: 71 - 2
Jiang W.Alford VC.Qiu Y.Bhattacharjee S.John TM.Johnson DH.Kraft PJ.Lundeen SG.Sui Z. Bioorg. Med. Chem. 2004, 12: 1505 - 3
Yamashkin SA.Yudin LG.Kost AN. Chem. Heterocycl. Compd. (Engl. Transl.) 1983, 19: 401 - 4
Kontogiorgis C.Litinas KE.Makri A.Nicolaides DN.Vronteli A.Litina DJH.Pontiki E.Siohou A. J. Enzyme Inhib. Med. Chem. 2008, 23: 43 - 5
Rodighiero P.Chilin A.Pastorini G.Guiotto A. J. Heterocycl. Chem. 1987, 24: 1041 - 6
Guiotto A.Chilin A.Manzini P.Dall’Acqua F.Bordin F.Rodighiero P. Farmaco 1995, 50: 479 - 7
Gia O.Mobilio S.Chilin A.Rodghiero P.Palumbo M. J. Photochem. Photobiol., B. 1988, 2: 435 - 8
Quanten E.Adriaens P.Schryver FC.Roelandts R.Degreef H. Photochem. Photobiol. 1986, 43: 485 - 9
Kontogiorgis C.Litinas KE.Makri A.Nicolaides DN.Vronteli A.Litina DJH.Pontiki E.Siohou A. J. Enzyme Inhib. Med. Chem. 2008, 23: 43 - 10
Chen L.Hu T.-S.Yao Z.-J. Eur. J. Org. Chem. 2008, 6175 - 11
Chen L.Xu MH. Adv. Synth. Catal. 2009, 351: 2005 -
12a
Ridley CP.Reddy MVR.Rocha G.Bushman FD.Faulknera DJ. Bioorg. Med. Chem. 2002, 10: 3285 -
12b
Fan H.Peng J.Hamann MT.Hu JH. Chem. Rev. 2008, 108: 264 -
12c
Yamaguchi T.Fukuda T.Ishibashi F.Iwao M. Tetrahedron Lett. 2006, 47: 3755 -
12d
Tardy C.Facompré M.Laine W.Baldeyrou B.García-Gravalos D.Francesch A.Mateo C.Pastor A.Jiménez JA.Manzanares I.Cuevasb C.Bailly C. Bioorg. Med. Chem. 2004, 12: 1697 - 13
Hiremath SP.Badiger GR.Jivanagi AS.Purohit MG. Indian J. Chem. 1992, 313: 583 -
14a
Kuethe JT.Wong A.Qu C.Smitrovich J.Davies IW.Hughes DL. J. Org. Chem. 2005, 70: 2555 -
14b
Van Zandt MC.Jones ML.Gunn DE.Geraci LS.Jones JH.Sawicki DR.Sredy J.Jacot JL.Dicioccio AT.Petrova T.Mitschler A.Podjarny AD. J. Med. Chem. 2005, 48: 3141 -
14c
Faulkner D. J. Nat. Prod. Rep. 1999, 16: 155 -
14d
Lounasmaa M.Tolvanen A. Nat. Prod. Rep. 2000, 17: 175 -
15a
Henry JR.Rupert KC.Dodd JH.Turchi IJ.Wadsworth SA.Cavender DE.Fahmy B.Olini GC.Davis JE.Pellegrino-Gensey JL.Schafer PH.Siekierka JJ. J. Med. Chem. 1998, 41: 4196 -
15b
Henry JR.Rupert KC.Dodd JH.Turchi IJ.Wadsworth SA.Cavender DE.Schafer PH.Siekierka J. J. Bioorg. Med. Chem. Lett. 1998, 8: 3335 - 16
Peter AN,Thomas B,Anna K,Tero L, andPeter S. inventors; WO 2004016609. ; Chem. Abstr. 2004, 140, 217627 - 17
Majumdar KC.Chattopadhyay B. Synthesis 2008, 921 - 18
Majumdar KC.Chattopadhyay B.Samanta S. Synthesis 2008, 311 - 19
Majumdar KC.Chakravorty S.Shyam PK.Taher A. Synthesis 2009, 403 - 20
Majumdar KC.Mondal S. Tetrahedron Lett. 2009, 49: 2418 - 21
Chen C.-Y.Lieberman DR.Larsen DR.Verhoeven TR.Reider PJ. J. Org. Chem. 1997, 62: 2676 -
23a
Rodriguez AL.Koradin C.Dohle W.Knochel P. Angew. Chem. Int. Ed. 2000, 39: 2488 -
23b
Koradin C.Dohle W.Rodriguez AL.Schmid B.Knochel P. Tetrahedron 2003, 59: 1571 -
23c
Amjad M.Knight DW. Tetrahedron Lett. 2004, 45: 539 -
23d
Cacchi S.Fabrizi G.Parisi LM. J. Comb. Chem. 2005, 7: 510 -
23e
Nazaré M.Schneider C.Lindenschmidt A.Will DW. Angew. Chem. Int. Ed. 2004, 43: 4256 -
23f
Roy PJ.Dufresne C.Lachance N.Leclerc J.-P.Boisvert M.Wang Z.Leblanc Y. Synthesis 2005, 2751 - 24
Blache Y.Sinibaldi-Troin M.-E.Hichour M.Benezech V.Chavignon O.Gramain J.-C.Teulade J.-C.Chapat J.-P. Tetrahedron 1999, 55: 1959 - 25
Lachance N.April M.Joly M.-A. Synthesis 2005, 2571 - 26
Xu Z.Hu W.Zhang F.Li Q.Lu Z.Zhang L.Jia Y. Synthesis 2008, 3981 - 27
Spergel SH.Danielle R.Okoro DR.Pitts W. J. Org. Chem. 2010, 75: 5316
References and Notes
General Procedure
for the Synthesis of Compound 3a by Heck Reaction
A
mixture of 1a (100 mg, 0.395 mmol), cyclohexanone
(2a, 77.5 mg, 0.79 mmol), and DABCO (132.7
mg, 1.185 mmol) was taken in DMF (5 mL) under nitrogen atmosphere. Pd(OAc)2 (10
mol%, 8.8 mg) was added and the reaction mixture was stirred
at 120 ˚C for 4 h. After completion of the reaction
as monitored by TLC, the reaction mixture was cooled, H2O
(20 mL) was added and extracted with EtOAc (3 × 30
mL). The EtOAc extract was washed with H2O (2 × 40
mL), followed by brine (30 mL). The organic layer was dried (Na2SO4),
and the solvent was evaporated to give a crude product which was
purified by column chromatog-raphy over silica gel (230-400
mesh) using PE-EtOAc (3:2) as eluent. Product 3a was isolated as a white solid in 91% yield.
Compound 3a
Yield 91%,
solid, mp 254-256 ˚C. IR (KBr): 1637,
3305 cm-¹. ¹H NMR
(400 MHz, CDCl3): δ = 8.30
(d, 1 H, J = 9.5 Hz),
8.00 (s, 1 H), 7.48 (d, 1 H, J = 9.0
Hz), 7.13 (d, 1 H, J = 9.0
Hz), 6.73 (d, 1 H, J = 9.5
Hz), 3.80 (s, 3 H), 3.00 (br s, 2 H), 2.80 (br s, 2 H), 1.93 (br
s, 4 H). ¹³C NMR (100 MHz, DMSO): δ = 22.17,
23.13, 23.18, 23.41, 29.57, 107.28, 108.69, 112.51, 114.75, 118.38,
122.47, 130.57, 134.79, 135.60, 136.82, 160.65; MS: m/z = 253 [M+ + H].
Anal. Calcd for C16H16N2O: C, 76.16;
H, 6.39; N, 11.10. Found: C, 76.34, H, 6.42, N, 11.27.