References and Notes
-
1a
Multicomponent
Reactions
Zhu J.
Bienaymé H.
Wiley-WCH;
Weinheim:
2006.
-
1b
Ganem B.
Acc.
Chem. Res.
2009,
42:
463
-
2a
Orru RVA.
de Greef M.
Synthesis
2003,
1471
-
2b
D’Souza DM.
Müller TJJ.
Chem. Soc. Rev.
2007,
36:
1095
-
2c
Sunderhaus JD.
Martin SF.
Chem.
Eur. J.
2009,
15:
1300
- 3
Toure BB.
Hall DG.
Chem. Rev.
2009,
109:
4439
-
4a
de Boer T.
Amore A.
Orru RVA. In Microwaves
in Organic Synthesis
2nd ed., Vol. 2:
Loupy A.
Wiley-VCH;
Weinheim:
2006.
p.788
-
4b
Caddick S.
Fitzmaurice R.
Tetrahedron
2009,
65:
3325
- 5
The
Chemistry of Heterocyclic Compounds: Isoquinolines
Part
3, Vol. 38:
Coppola GM.
Schuster HF.
John Wiley
and Sons;
New York:
1981.
-
Isoquinoline synthesis:
-
6a
Ghorai BK.
Duan S.
Jiang D.
Herndon JW.
Synthesis
2006,
3661
-
6b
Ghorai BK.
Jiang D.
Herndon JW.
Org. Lett.
2003,
5:
4261
-
6c
Shvartsberg MS.
Ivanchikova ID.
Vasilevsky SF.
Tetrahedron Lett.
1994,
35:
2077
-
6d
Sakamoto T.
Numata A.
Kondo Y.
Chem.
Pharm. Bull.
2000,
48:
669
-
6e
Tovar JD.
Swager TM.
J.
Org. Chem.
1999,
64:
6499
-
6f
Ohta YS.
Oishi Fujii N.
Ohno H.
Chem. Commun.
2008,
835
-
6g
Magnus P.
Matthews KS.
Lynch V.
Org.
Lett.
2003,
5:
2181
-
6h
Huang Q.
Larock RC.
J. Org. Chem.
2003,
68:
980
-
6i
Huang Q.
Larock RC.
Tetrahedron Lett.
2002,
43:
3557
-
6j
Dai G.
Larock RC.
J. Org. Chem.
2003,
68:
920
-
6k
Dai G.
Larock
RC.
Org. Lett.
2001,
3:
4035
-
6l
Dai G.
Larock RC.
J. Org.
Chem.
2002,
67:
7042
-
6m
Dai G.
Larock RC.
Org. Lett.
2002,
4:
193
-
6n
Huang Q.
Hunter JA.
Larock RC.
J. Org. Chem.
2002,
67:
3437
-
6o
Huang Q.
Hunter JA.
Larock RC.
Org. Lett.
2001,
3:
2973
-
6p
Roesch KR.
Larock RC.
J.
Org. Chem.
2002,
67:
86
-
6q
Roesch KR.
Larock RC.
Org.
Lett.
1999,
1:
553
-
Dihydroisoquinolines synthesis:
-
7a
Gao K.
Wu J.
J. Org. Chem.
2007,
72:
8611
-
7b
Ding Q.
Wang B.
Wu J.
Tetrahedron
2007,
35:
12166
-
7c
Asao N.
Iso K.
Yuda SS.
Org.
Lett.
2006,
8:
4149
-
7d
Sun W.
Ding Q.
Sun X.
Fan R.
Wu J.
J. Comb. Chem.
2007,
9:
690
-
7e
Ding Q.
Wu J.
Org. Lett.
2007,
9:
4959
-
7f
Ye Y.
Ding Q.
Wu J.
Tetrahedron
2008,
64:
1378
-
7g
Iso K.
Salprima YS.
.
Asao N.
Heterocycles
2007,
74:
649
-
7h
Iso K.
Yudha SS.
Asao N.
Synthesis
2008,
820
-
7i
Ding Q.
Yu X.
Wu J.
Tetrahedron
Lett.
2008,
49:
2752
-
7j
Su S.
Porco JA.
J. Am.
Chem. Soc.
2007,
129:
7744
-
7k
Obika S.
Kono H.
Yasui Y.
Yanada R.
Takemoto Y.
J. Org.
Chem.
2007,
72:
4462
-
7l
Yanada R.
Obika S.
Kono H.
Takemoto Y.
Angew. Chem. Int. Ed.
2006,
45:
3822
-
7m
Asao N.
Yuda SS.
Nogami T.
Yamamoto Y.
Angew. Chem. Int. Ed.
2005,
44:
5526
-
7n
Nakamura H.
Saito H.
Nanjo M.
Tetrahedron
Lett.
2008,
49:
2697
-
7o
Ohtaka M.
Nakamura H.
Yamamoto Y.
Tetrahedron
Lett.
2004,
45:
7339
-
8a
Ohta Y.
Kubota Y.
Watabe T.
Chiba H.
Oishi S.
Fujii N.
Ohno H.
J.
Org. Chem.
2009,
74:
6299
-
8b
Sha F.
Huang X.
Angew. Chem. Int. Ed.
2009,
48:
3458
- 9
Zhou H.
Jin H.
Ye S.
He X.
Wu J.
Tetrahedron Lett.
2009,
50:
4616
-
10a
Ahmed MSM.
Kobayashi K.
Mori A.
Org. Lett.
2005,
7:
4487
-
10b
Willy B.
Müller TJJ.
Eur.
J. Org. Chem.
2008,
4157
- 11
Willy B.
Rominger F.
Müller TJJ.
Synthesis
2008,
293
-
12a
Karpov AS.
Merkul E.
Oeser T.
Müller TJJ.
Chem. Commun.
2005,
2581
-
12b
Karpov AS.
Merkul E.
Oeser T.
Müller TJJ.
Eur.
J. Org. Chem.
2006,
2991
-
13a
Yehia NAM.
Polborn K.
Müller TJJ.
Tetrahedron Lett.
2002,
43:
6907
-
13b
Dediu OG.
Yehia NAM.
Oeser T.
Polborn K.
Müller TJJ.
Eur.
J. Org. Chem.
2005,
1834
-
13c
Schramm OG.
Oeser T.
Müller TJJ.
J. Org. Chem.
2006,
71:
3494
-
14a
Karpov AS.
Müller TJJ.
Org. Lett.
2003,
5:
3451
-
14b
Karpov AS.
Müller TJJ.
Synthesis
2003,
2815
-
14c
Karpov AS.
Merkul E.
Rominger F.
Müller TJJ.
Angew.
Chem. Int. Ed.
2005,
44:
6951
- 15
Kaspar LT.
Ackermann L.
Tetrahedron
2005,
61:
11311
- 16
Rotaru AV.
Druta ID.
Oeser T.
Müller TJJ.
Helv. Chim.
Acta
2005,
88:
1798
- 17
Bossharth E.
Desbordes P.
Monteiro N.
Balme G.
Org. Lett.
2003,
5:
2441
- 18
Willy B.
Müller TJJ.
Synlett
2009,
1255
- 19
Willy B.
Frank W.
Müller TJJ.
Org. Biomol. Chem.
2010,
8:
90
-
20a
Karpov AS.
Oeser T.
Müller TJJ.
Chem.
Commun.
2004,
1502
-
20b
Karpov AS.
Rominger F.
Müller TJJ.
Org. Biomol. Chem.
2005,
3:
4382
-
21a
Arcadi A.
Rossi E.
Synlett
1997,
667
-
21b
Arcadi A.
Rossi E.
Tetrahedron
1998,
54:
15253
-
21c
Arcadi A.
Attanasi OA.
Guidi B.
Rossi E.
Santeusanio S.
Chem. Lett.
1999,
59
-
21d
Arcadi A.
Attanasi OA.
Guidi B.
Santeusanio S.
Rossi E.
Eur.
J. Org. Chem.
1999,
3117
-
21e
Abbiati G.
Beccalli E.
Marchesini A.
Rossi E.
Synthesis
2001,
2477
-
22a
Abbiati G.
Arcadi A.
Bellinazzi A.
Beccalli E.
Rossi E.
Zanzola S.
J.
Org. Chem.
2005,
70:
4088
-
22b
Abbiati G.
Arcadi A.
Beccalli E.
Rossi E.
Tetrahedron Lett.
2003,
44:
5331
- 23
Alfonsi M.
Dell’Acqua M.
Facoetti D.
Arcadi A.
Abbiati G.
Rossi E.
Eur. J. Org. Chem.
2009,
2852
- 24
Microwaves
in Organic Synthesis
2nd ed.:
Loupy A.
Wiley-VCH;
Weinheim:
2006.
-
25a
Mori A.
Mohamed Ahmed MS.
Sekiguki A.
Masui K.
Koike T.
Chem. Lett.
2002,
756
-
25b
Mohamed Ahmed MSM.
Mori A.
Org.
Lett.
2003,
5:
3057
-
25c
Ahmed
MSM.
Mori A.
Tetrahedron
2004,
60:
9977
-
26a
Asao N.
Nogami T.
Takahashi K.
Yamamoto Y.
J.
Am. Chem. Soc.
2002,
124:
764
-
26b
Wei L.-L.
Wei
L.-M.
Pan W.-B.
Wu M.-J.
Synlett
2004,
1497
-
26c
Patil NT.
Yamamoto Y.
J. Org.
Chem.
2004,
69:
5139
-
26d
Mondal S.
Nogami T.
Asao N.
Yamamoto Y.
J. Org. Chem.
2003,
68:
9496
- 27
Godet T.
Vaxelaire C.
Michel C.
Milet A.
Belmont P.
Chem.
Eur. J.
2007,
13:
5632
- 28
Gulías M.
Rodríguez JR.
Castedo L.
Mascareñas JL.
Org.
Lett.
2003,
5:
1975
-
For some representative examples,
see:
-
29a
Alami M.
Ferri F.
Linstrumelle G.
Tetrahedron
Lett.
1993,
34:
6403
-
29b
Leadbeater NE.
Tominack BJ.
Tetrahedron
Lett.
2003,
44:
8653
-
29c
Gil-Moltó J.
Nájera C.
Eur.
J. Org. Chem.
2005,
4073
-
29d
Bakherad M.
Keivanloo A.
Bahramian B.
Mihanparast S.
Tetrahedron Lett.
2009,
50:
6418
- 30
Mori A.
Kawashima J.
Shimada T.
Suguro M.
Hirabayashi K.
Nishihara Y.
Org. Lett.
2000,
2:
2935
- 32
Yamamoto Y.
J.
Org. Chem.
2007,
72:
7817
31
Synthesis of 3-(4-Methoxyphenyl)isoquinoline
(3d)
In a sealed MW test tube, to a solution of 2-bromobenz-aldehyde
(1a, 185 mg, 0.116 mL, 1 mmol) in THF (1
mL), 4-ethynylanisole (159 mg, 0.156 mL, 1.2 mmol), and trans-dichlorobis(triphenylphosphine)palladium
(7.02 mg, 0.01 mmol) were added. The solution was stirred at r.t.
for 10 min, then NH3 (2.5 M aq, 3 mL) and CuI (3.81 mg,
0.02 mmol) were added. The stirred reaction mixture was heated at
130 ˚C (max. power setting = 500
W) in a multimode microwave oven (Microsinth Milestone®)
for 2 h. The reaction mixture was diluted with H2O (70
mL) and extracted with EtOAc (3 × 70
mL). The organic layer dried with Na2SO4,
was evaporated to dryness, and the crude material was purified by
flash chromatography over a silica gel column (hexane-EtOAc = 96:4)
yielding the isoquinoline 3d (132 mg, 56%)
as brown solid; mp 85-87 ˚C. IR (KBr):
1626, 1606, 1584, 1512, 1447, 1292, 1249, 1179, 1024, 834 cm-¹. ¹H
NMR (200 MHz, CDCl3): δ = 3.88 (s,
3 H, CH3), 7.04 (d, 2 H, arom, J = 8.8
Hz), 7.57 (ddd, 1 H, arom, J = 8.1,
7.0, 1.1 Hz), 7.67 (ddd, 1 H, arom, J = 8.4, 7.0,
1.5 Hz), 7.85 (d, 1 H, arom, J = 8.1
Hz), 7.95-7.99 (m, 2 H, arom), 8.08 (d, 2 H, arom, J = 8.8 Hz),
9.31 (s, 1 H, arom). ¹³C NMR (50.3
MHz, CDCl3): δ = 55.6
(CH3), 114.5, 115.5, 126.8, 126.9, 127.8, 128.4, 130.6,
152.5 (CH arom), 127.7, 132.6, 137.0, 151.4, 160.5 (C quat.). ESI-MS: m/z (%) = 236
(100) [M + 1]+. Anal.
Calcd for C16H13NO (235.28): C, 81.68; H,
5.57; N, 5.95. Found: C, 81.77; H, 5.60; N, 5.93.
