References and Notes
For reviews, see:
1a
Wolfe JP.
Wagaw S.
Marcoux J.-F.
Buchwald SL.
Acc. Chem. Res.
1998,
31:
805
1b
Hartwig JF.
Angew. Chem. Int. Ed.
1998,
37:
2046
2a
Sigman MS.
Schultz MJ.
Org. Biomol. Chem.
2004,
2:
2551
2b
Bar GLJ.
Lloyd-Jones GC.
Booker-Milburn KI.
J. Am. Chem. Soc.
2005,
127:
7308
2c
Brice JL.
Harang JE.
Timokhin VI.
Anastasi NR.
Stahl SS.
J. Am. Chem. Soc.
2005,
127:
2868
2d
Timokhin VI.
Anastasi NR.
Stahl SS.
J. Am. Chem. Soc.
2003,
125:
12996
2e
Gowan M.
Caillé AS.
Lau CK.
Synlett
1997,
1312
2f
Andersson PG.
Bäckvall J.-E.
J. Am. Chem. Soc.
1992,
114:
8696
2g
Bäckvall J.-E.
Andersson PG.
J. Am. Chem. Soc.
1990,
112:
3683
2h
Pugin B.
Venanzi LM.
J. Am. Chem. Soc.
1983,
105:
6877
2i
Hegedus LS.
Allen GF.
Bozell JJ.
Waterman EL.
J. Am. Chem. Soc.
1978,
100:
5800
3
Li JJ.
Gribble GW.
Palladium in Heterocyclic Chemistry, A Guide for the Synthetic Chemist
Pergamon;
New York:
2000.
For recent contributions, see:
4a
Cacchi S.
Fabrizi G.
Chem. Rev.
2005,
105:
2873
4b
Capito E.
Brown JM.
Ricci A.
Chem. Commun.
2005,
1854
4c
Grimster NP.
Gauntlett C.
Godfrey CRA.
Gaunt MJ.
Angew. Chem. Int. Ed.
2005,
44:
3125
4d
Cacchi S.
Fabrizi G.
Parisi LM.
Synthesis
2004,
1889
4e
Siebeneicher H.
Bytschkov I.
Doye S.
Angew. Chem. Int. Ed.
2003,
42:
3042
4f
Willis MC.
Brace GN.
Holmes IP.
Angew. Chem. Int. Ed.
2005,
44:
403
4g
Watanabe T.
Arai S.
Nishida A.
Synlett
2004,
907
5a
Sundberg RJ.
Indoles
Academic Press;
London:
1996.
5b
Knölker H.-J.
Reddy KR.
Chem. Rev.
2002,
102:
4303
5c
Gilchrist TL.
J. Chem. Soc., Perkin Trans. 1
1999,
2848
5d
Gribble GW.
J. Chem. Soc., Perkin Trans. 1
2000,
1045
5e
Bräse S.
Gil C.
Knepper K.
Bioorg. Med. Chem.
2002,
10:
2415
6a
Beccalli EM.
Broggini G.
Marchesini A.
Rossi E.
Tetrahedron
2002,
58:
6673
6b
Beccalli EM.
Broggini G.
Tetrahedron Lett.
2003,
44:
1919
6c
Abbiati G.
Beccalli EM.
Broggini G.
Zoni C.
J. Org. Chem.
2003,
68:
7625
6d Abbiati, G.; Beccalli, E. M.; Broggini, G.; Paladino, G.; Rossi, E. Synthesis, in press.
7a
Tiwari RK.
Singh J.
Singh D.
Verma AK.
Chandra R.
Tetrahedron
2005,
61:
9513
7b
Abbiati G.
Arcadi A.
Bellinazzi A.
Beccalli EM.
Rossi E.
Zanzola S.
J. Org. Chem.
2005,
70:
4088
8a Ruppelt M, Bartel S, Guarnieri W, Raddatz S, Rosentreter U, Wild H, Endermann R, and Kroll HP. inventors; Ger. Offen. DE 19802235.
; Chem. Abstr. 1999, 131, 129985
9a Davis PD, Hill CH, and Lawton G. inventors; Eur. Pat. 384349.
; Chem. Abstr. 1991, 114, 81582p
9b
Bit RA.
Davis PD.
Elliott LH.
Harris W.
Hill CH.
Keech E.
Kumar H.
Lawton G.
Maw A.
Nixon JS.
Vesey DR.
Wadsworth J.
Wilkinson SE.
J. Med. Chem.
1993,
36:
21
10
Wyss PC.
Gerber P.
Hartman PG.
Hubschwerlen C.
Locher H.
Marty H.-P.
Stahl M.
J. Med. Chem.
2003,
46:
2304
11 McCort G, Hoornaert C, Duclos O, Guilpain E, Cadilhac C, and Dellac G. inventors; Fr. Patent FR 2 761 073.
; Chem. Abstr. 1999, 130, 384000
12
Tapia RA.
Prieto Y.
Pautet F.
Domard M.
Sarciron M.-E.
Walchshofer N.
Fillion H.
Eur. J. Org. Chem.
2002,
4005
13
Vigushin DM.
Brooke G.
Willows D.
Coombes RC.
Moody CJ.
Bioorg. Med. Chem. Lett.
2003,
13:
3661
14
Chang-Fong J.
Addo J.
Dukat M.
Smith C.
Mitchell NA.
Herrick-Davis K.
Teitler M.
Glennon RA.
Bioorg. Med. Chem. Lett.
2002,
12:
155
15
Padwa A.
Hertzog DL.
Nadler WR.
Osterhout MH.
Price AT.
J. Org. Chem.
1994,
59:
1418
16
Experimental Procedure.
A suspension of 2a (276 mg, 1.0 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), Na2CO3 (318 mg, 3.0 mmol), Bu4NCl (278 mg, 1.0 mmol) and p-benzoquinone (108 mg, 1 mmol) in DMF (10 mL) was stirred for 24 h at 100 °C. The solution was washed with brine (25 mL) and extracted with Et2O (2 × 25 mL). The organic layer was dried over Na2SO4 and taken to dryness under reduced pressure. The residue was chromatographed on a silica gel column with light PE-EtOAc 12:1 as eluent to give 3a.
Data for 3-Methyl-2-phenyl-2
H
-pyrazino[1,2-
a
]indol-1-one (3a).
Mp 249-250 °C (diisopropyl ether). IR (nujol): 1682 cm-1. 1H NMR (400 MHz, CDCl3): δ = 1.95 (3 H, s), 7.24 (1 H, s), 7.29-7.34 (3 H, m), 7.39-7.45 (2 H, m), 7.48-7.56 (3 H, m), 7.68 (1 H, d, J = 8.2 Hz), 7.85 (1 H, d, J = 8.1 Hz). 13C NMR (100 MHz, CDCl3): δ = 18.7 (q), 103.5 (d), 104.1 (d), 110.8 (d), 122.6 (d), 123.0 (s), 123.1 (d), 124.3 (d), 127.4 (s), 128.0 (s), 129.1 (d), 129.4 (d), 129.9 (d), 132.3 (s), 137.9 (s), 158.4 (s). MS: m/z = 274 [M+]. Anal. Calcd for C18H14N2O: C, 78.81; H, 5.14; N, 10.21. Found: C, 78.97; H, 4.99; N, 10.32.
17
Jeffery T.
Tetrahedron
1996,
30:
10113
18
3-Methyl-2-(pyridin-2-yl)-3,4-dihydro-2
H
-pyrazino[1,2-
a
]indol-1-one (8).
Mp 198-199 °C (diisopropyl ether). IR (nujol): 1678 cm-1. 1H NMR (400 MHz, CDCl3): δ = 1.46 (3 H, d, J = 6.7 Hz), 4.32 (1 H, d, J = 12.0 Hz), 4.44 (1 H, dd, J = 4.0, 12.0 Hz), 5.43-5.51 (1 H, m), 7.13 (1 H, dd, J = 5.0, 7.0 Hz), 7.18-7.24 (1 H, m), 7.34-7.44 (2 H, m), 7.45 (1 H, s), 7.71-7.80 (2 H, m), 8.17 (1 H, d, J = 8.4 Hz), 8.47 (1 H, d, J = 4.0 Hz). 13C NMR (100 MHz, CDCl3): δ = 19.3 (q), 46.4 (t), 51.5 (d), 107.9 (d), 110.1 (d), 120.1 (d), 120.7 (d), 121.2 (d), 123.2 (d), 125.3 (d), 128.0 (s), 129.2 (s), 137.3 (s), 137.7 (d), 148.1 (d), 152.9 (s), 159.7 (s). MS: m/z = 277 [M+]. Anal. Calcd for C17H15N3O: C, 73.63; H, 5.45; N, 15.15. Found: C, 73.51; H, 5.27; N, 15.01.
19
Chacun-Lefèvre L.
Bénéteau V.
Joseph B.
Mérour J.-Y.
Tetrahedron
2002,
58:
10181
20
2-Methyl-12,12a-dihydro-1
H
-pyrrolo[1′,2′:4,5]pyr-azino[1,2-
a
]indol-5-one (10).
Oil. IR (nujol): 1657 cm-1. 1H NMR (400 MHz, DMSO): δ = 1.83 (3 H, s), 2.59-2.69 (1 H, m), 2.78 (1 H, dd, J = 9.2, 15.9 Hz), 3.97 (1 H, dd, J = 12.1, 12.2 Hz), 4.52-4.65 (1 H, m), 4.92 (1 H, dd, J = 4.4, 12.1 Hz), 6.80 (1 H, s), 7.08 (1 H, s), 7.12 (1 H, dd, J = 7.7, 8.3 Hz), 7.31 (1 H, dd, J = 7.7, 8.0 Hz), 7.57 (1 H, d, J = 8.3 Hz), 7.67 (1 H, d, J = 8.0 Hz). 13C NMR (100 MHz, DMSO): δ = 14.4 (q), 38.8 (t), 45.9 (t), 57.5 (d), 106.6 (d), 109.9 (d), 116.6 (d), 121.1 (d), 122.6 (s), 123.2 (d), 125.0 (d), 128.0 (s), 129.6 (s), 136.8 (s), 169.7 (s). MS: m/z 238 [M+]. Anal. Calcd for C15H14N2O: C, 75.61; H, 5.92; N, 11.76. Found: C, 75.79; H, 6.01; N, 11.92.
21a
Kasahara A.
Izumi T.
Murakami S.
Miyamoto K.
Hino T.
J. Heterocycl. Chem.
1989,
26:
1405
21b
Izumi T.
Nishimoto Y.
Kohei K.
Kasahara A.
J. Heterocycl. Chem.
1990,
27:
1419
22a
Alexanian EJ.
Lee C.
Sorensen EJ.
J. Am. Chem. Soc.
2005,
127:
7690
22b
Beccalli EM.
Broggini G.
Paladino G.
Penoni A.
Zoni C.
J. Org. Chem.
2004,
69:
5627
22c
Fix SR.
Brice JL.
Stahl SS.
Angew. Chem. Int. Ed.
2002,
41:
164
22d
Larock RC.
Hightower TR.
Hasvold LA.
Peterson KP.
J. Org. Chem.
1996,
61:
3584
22e
Rönn M.
Bäckvall J.-E.
Andersson PG.
Tetrahedron Lett.
1995,
36:
7749
22f
Hegedus LS.
McKearin JM.
J. Am. Chem. Soc.
1982,
104:
2444