References and Notes
1a
Cheeseman GW.
Cookson RF. In
The Chemistry of Heterocyclic
Compounds
2nd ed.:
Weissberger A.
Taylor EC.
Wiley;
New
York:
1979.
p.1
1b
Toshima K.
Ozawa T.
Kimura T.
Matsumura S.
Bioorg. Med. Chem. Lett.
2004,
14:
2777
1c
Carta A.
Paglietti G.
Nikookar MER.
Sanna P.
Sechi L.
Zanetti S.
Eur. J. Med. Chem.
2002,
37:
355
2a
Piras S.
Loriga M.
Paglietti G.
Farmaco
2004,
59:
185
2b
Carta A.
Loriga M.
Zanetti S.
Sechi LA.
Farmaco
2003,
58:
1251
3
Ali MM.
Ismail MMF.
El-Gaby MSA.
Zahran
MA.
Ammar YA.
Molecules
2000,
5:
864
4
Sarges R.
Howard HR.
Browne RG.
Lebel LA.
Seymour PA.
Koe BK.
J.
Med. Chem.
1990,
33:
2240
5
Sakata G.
Makino K.
Kurasawa Y.
Heterocycles
1998,
27:
2481
6
Gomtsyan A.
Bayburt EK.
Schmidt RG.
Zeng GZ.
Perner RJ.
Didomenico S.
Koenig JR.
Turner S.
Jinkerson T.
Drizin I.
Hannick SM.
Macri BS.
McDonald HA.
Honore P.
Wismer CT.
Marsh KC.
Wetter J.
Stewart KD.
Oie T.
Jarvis MF.
Surowy
CS.
Faltynek CR.
Lee C.-H.
J.
Med. Chem.
2005,
48:
744
7
Seitz LE.
Suling WJ.
Reynolds RC.
J. Med. Chem.
2002,
45:
5604
8
Jaso A.
Zarranz B.
Aldana I.
Monge A.
J.
Med. Chem.
2005,
48:
2019
9
He W.
Myers MR.
Hanney B.
Spada AP.
Bilder G.
Galzcinski H.
Amin D.
Needle S.
Page K.
Jayyosi Z.
Perrone MH.
Bioorg. Med. Chem. Lett.
2003,
13:
3097
10
Kim YB.
Kim YH.
Park JY.
Kim SK.
Bioorg. Med. Chem. Lett.
2004,
14:
541
11
Myers MR.
He W.
Hanney B.
Setzer N.
Maguire
MP.
Zulli A.
Bilder G.
Galzcinski H.
Amin D.
Needle S.
Spada AP.
Bioorg. Med. Chem.
Lett.
2003,
13:
3091
12
Pearlman WM.
Org.
Synth.
1969,
49:
75
13a
Katoh A.
Yoshida T.
Ohkanda J.
In Heterocycles
2000,
52:
911
13b
Thomas KRJ.
Velusamy M.
Lin
JT.
Chuen C.-H.
Tao Y.-T.
Chem. Mater.
2005,
17:
1860
13c
Dailey S.
Feast WJ.
Peace RJ.
Sage IC.
Till S.
Wood EL.
J. Mater. Chem.
2001,
11:
2238
13d
Sascha O.
Rüdiger F.
Synlett
2004,
1509
13e
Sessler JL.
Maeda H.
Mizuno T.
Lynch VM.
Furuta H.
J. Am. Chem. Soc.
2002,
124:
13474
13f
Crossley MJ.
Johnston LA.
Chem.
Commun.
2002,
1122
14a
Brown DJ.
Quinoxalines Supplements
II, In The Chemistry of Heterocyclic Compounds
Taylor EC.
Wipf P.
John Wiley & Sons;
New
Jersey:
2004.
14b
Bhosale RS.
Sarda SR.
Ardhapure SS.
Jadhav
WN.
Bhusare SR.
Pawar RP.
Tetrahedron Lett.
2005,
46:
7183
14c
More SV.
Sastry MNV.
Yao C.-F.
Green Chem.
2006,
8:
91
14d
Zhao Z.
Wisnoski DD.
Wolkenberg SE.
Leister WH.
Wang Y.
Lindsley
CW.
Tetrahedron
Lett.
2004,
45:
4873
15
Aparicio D.
Attanasi OA.
Filippone P.
Ignacio R.
Lillini S.
Mantellini F.
Palacios F.
De los Santos JM.
J.
Org. Chem.
2006,
71:
5897
16a
Raw SA.
Wilfred CD.
Taylor RJK.
Org. Biomol. Chem.
2004,
2:
788
16b
Kim SY.
Park KH.
Chung
YK.
Chem. Commun.
2005,
1321
16c
Robinson RS.
Taylor RJK.
Synlett
2005,
1003
16d
Cho CS.
Oh SG.
J.
Mol. Catal. A: Chem.
2007,
276:
205
16e
Shaabani A.
Maleki A.
Chem. Pharm. Bull.
2008,
56:
79
17a
Singh SK.
Gupta P.
Duggineni S.
Kundu B.
Synlett
2003,
2147
17b
Das B.
Venkateswarlu K.
Suneel K.
Majhi A.
Tetrahedron Lett.
2007,
48:
5371
18
Cho CS.
Oh SG.
Tetrahedron Lett.
2006,
47:
5633
19a
Antoniotti S.
Duñach E.
Tetrahedron
Lett.
2002,
43:
3971
19b
Nasar MK.
Kumar RR.
Perumal S.
Tetrahedron Lett.
2007,
48:
2155
20
Cho CS.
Ren WX.
Shim SC.
Tetrahedron
Lett.
2007,
48:
4665
21
Krasavin M.
Parchinsky V.
Synlett
2008,
645
22a
Dömling A.
Ugi I.
Angew.
Chem. Int. Ed.
2000,
39:
3168
22b
Dömling A.
Chem. Rev.
2006,
106:
17
22c
Tietze LF.
Chem. Rev.
1996,
96:
115
22d
Posner
GH.
Chem. Rev.
1986,
86:
831
22e
Ramón DJ.
Yus M.
Angew.
Chem. Int. Ed.
2005,
44:
1602
23
Bienaymé H.
Hulme C.
Oddon G.
Schmitt P.
Chem. Eur. J.
2000,
6:
3321
24a
Van Leusen D.
Van Leusen AM.
Org.
React.
2001,
57:
417
24b
Tandon VK.
Rai S.
Sulfur Reports
2003,
24:
307
25a
Denmark SE.
Fan Y.
J.
Org. Chem.
2005,
70:
9667
25b
Krishna PR.
Dayaker G.
Reddy PVN.
Tetrahedron Lett.
2006,
47:
5977
26a
Sisko J.
Kassick AJ.
Mellinger M.
Filan JJ.
Allen A.
Olsen MA.
J.
Org. Chem.
2000,
65:
1516
26b
Ten-Have R.
Huisman M.
Meetsma A.
Van Leusen AM.
Tetrahedron
1997,
33:
11355
26c
Beck B.
Leppert CA.
Mueller BK.
Dömling A.
QSAR
Com. Sci.
2006,
25:
527
27
Terzidis M.
Tsoleridis CA.
Stephanidou-Stephanatou J.
Tetrahedron
2007,
63:
7828
28 Evolution of gas with alkaline pH
and characteristic amine odor was detected.
29 All melting points were determined
on a Büchi apparatus and are uncorrected. The ¹H
NMR and ¹³C NMR spectra were recorded
on a Bruker AM 300 spectrometer in CDCl3 with TMS as
internal standard. All coupling constants are given in Hz and chemical
shifts are given in ppm.
Typical Experimental
Procedure for the Preparation of 3e: To a stirred solution
of o-phenylenediamine (1a;
1.0 mmol) in toluene (20 mL), 4-chlorobenzaldehyde (1.0 mmol) was
added and stirring was continued for 5 min. Then TosMIC (1.0 mmol)
and DABCO (1.2 mmol) were added and the reaction mixture was heated
to 80 ˚C for 4 h. The resulting solution was initially
washed with 5% HCl, then with H2O and dried.
The solvent was distilled off under reduced pressure to yield the
corresponding crude product mixture, which was purified by silica
gel chromatography using petroleum ether-EtOAc (10:1) as
eluent, to give quinoxaline 3e in 84% yield;
yellow crystals; mp 136-
137 ˚C (ethanol)
(lit.
[³0]
137 ˚C). ¹H
NMR: δ = 7.51 (dd, J = 8.8,
2.1 Hz, 2 H, 3′-H, 5′-H), 7.74 (dd, J = 8.8, 2.1 Hz, 1 H, 7-H),
[³¹]
7.77 (dd, J = 8.8, 2.1 Hz, 1 H, 6-H),
8.10 (dd, J = 8.8, 2.1 Hz, 1
H, 5-H), 8.11 (dd, J = 8.8,
2.1 Hz, 1 H, 8-H), 8.12 (dd, J = 8.8,
2.0 Hz, 2 H, 2′-H, 6′-H), 9.27 (s, 1 H, 3-H).
¹³C
NMR: δ = 128.7 (C-2′, C-6′),
129.1 (C-5), 129.4 (C-3′, C-5′), 129.5 (C-8),
129.8 (C-7), 130.4 (C-6), 135.1 (C-1′), 136.5 (C-4′),
141.6 (C-4a), 142.1 (C-8a), 150.5 (C-2). Anal. Calcd for C14H9ClN2 (240.69):
C, 69.85; H, 3.74; N, 11.64. Found: C, 70.01; H, 3.83; N, 11.68.
30
Higashino T.
Takemoto M.
Tanji K.-I.
Iijima C.
Hayashi E.
Chem.
Pharm. Bull.
1985,
33:
4193
31 The multiplicities and chemical shifts
of the aromatic protons have been confirmed after simulation with
program SpinWorks, version 2.5, available from
ftp://davinci.chem.umanitoba.ca.
