References and Notes
<A NAME="RD29508ST-1A">1a</A>
Cheeseman GW.
Cookson RF. In
The Chemistry of Heterocyclic
Compounds
2nd ed.:
Weissberger A.
Taylor EC.
Wiley;
New
York:
1979.
p.1
<A NAME="RD29508ST-1B">1b</A>
Toshima K.
Ozawa T.
Kimura T.
Matsumura S.
Bioorg. Med. Chem. Lett.
2004,
14:
2777
<A NAME="RD29508ST-1C">1c</A>
Carta A.
Paglietti G.
Nikookar MER.
Sanna P.
Sechi L.
Zanetti S.
Eur. J. Med. Chem.
2002,
37:
355
<A NAME="RD29508ST-2A">2a</A>
Piras S.
Loriga M.
Paglietti G.
Farmaco
2004,
59:
185
<A NAME="RD29508ST-2B">2b</A>
Carta A.
Loriga M.
Zanetti S.
Sechi LA.
Farmaco
2003,
58:
1251
<A NAME="RD29508ST-3">3</A>
Ali MM.
Ismail MMF.
El-Gaby MSA.
Zahran
MA.
Ammar YA.
Molecules
2000,
5:
864
<A NAME="RD29508ST-4">4</A>
Sarges R.
Howard HR.
Browne RG.
Lebel LA.
Seymour PA.
Koe BK.
J.
Med. Chem.
1990,
33:
2240
<A NAME="RD29508ST-5">5</A>
Sakata G.
Makino K.
Kurasawa Y.
Heterocycles
1998,
27:
2481
<A NAME="RD29508ST-6">6</A>
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
<A NAME="RD29508ST-7">7</A>
Seitz LE.
Suling WJ.
Reynolds RC.
J. Med. Chem.
2002,
45:
5604
<A NAME="RD29508ST-8">8</A>
Jaso A.
Zarranz B.
Aldana I.
Monge A.
J.
Med. Chem.
2005,
48:
2019
<A NAME="RD29508ST-9">9</A>
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
<A NAME="RD29508ST-10">10</A>
Kim YB.
Kim YH.
Park JY.
Kim SK.
Bioorg. Med. Chem. Lett.
2004,
14:
541
<A NAME="RD29508ST-11">11</A>
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
<A NAME="RD29508ST-12">12</A>
Pearlman WM.
Org.
Synth.
1969,
49:
75
<A NAME="RD29508ST-13A">13a</A>
Katoh A.
Yoshida T.
Ohkanda J.
In Heterocycles
2000,
52:
911
<A NAME="RD29508ST-13B">13b</A>
Thomas KRJ.
Velusamy M.
Lin
JT.
Chuen C.-H.
Tao Y.-T.
Chem. Mater.
2005,
17:
1860
<A NAME="RD29508ST-13C">13c</A>
Dailey S.
Feast WJ.
Peace RJ.
Sage IC.
Till S.
Wood EL.
J. Mater. Chem.
2001,
11:
2238
<A NAME="RD29508ST-13D">13d</A>
Sascha O.
Rüdiger F.
Synlett
2004,
1509
<A NAME="RD29508ST-13E">13e</A>
Sessler JL.
Maeda H.
Mizuno T.
Lynch VM.
Furuta H.
J. Am. Chem. Soc.
2002,
124:
13474
<A NAME="RD29508ST-13F">13f</A>
Crossley MJ.
Johnston LA.
Chem.
Commun.
2002,
1122
<A NAME="RD29508ST-14A">14a</A>
Brown DJ.
Quinoxalines Supplements
II, In The Chemistry of Heterocyclic Compounds
Taylor EC.
Wipf P.
John Wiley & Sons;
New
Jersey:
2004.
<A NAME="RD29508ST-14B">14b</A>
Bhosale RS.
Sarda SR.
Ardhapure SS.
Jadhav
WN.
Bhusare SR.
Pawar RP.
Tetrahedron Lett.
2005,
46:
7183
<A NAME="RD29508ST-14C">14c</A>
More SV.
Sastry MNV.
Yao C.-F.
Green Chem.
2006,
8:
91
<A NAME="RD29508ST-14D">14d</A>
Zhao Z.
Wisnoski DD.
Wolkenberg SE.
Leister WH.
Wang Y.
Lindsley
CW.
Tetrahedron
Lett.
2004,
45:
4873
<A NAME="RD29508ST-15">15</A>
Aparicio D.
Attanasi OA.
Filippone P.
Ignacio R.
Lillini S.
Mantellini F.
Palacios F.
De los Santos JM.
J.
Org. Chem.
2006,
71:
5897
<A NAME="RD29508ST-16A">16a</A>
Raw SA.
Wilfred CD.
Taylor RJK.
Org. Biomol. Chem.
2004,
2:
788
<A NAME="RD29508ST-16B">16b</A>
Kim SY.
Park KH.
Chung
YK.
Chem. Commun.
2005,
1321
<A NAME="RD29508ST-16C">16c</A>
Robinson RS.
Taylor RJK.
Synlett
2005,
1003
<A NAME="RD29508ST-16D">16d</A>
Cho CS.
Oh SG.
J.
Mol. Catal. A: Chem.
2007,
276:
205
<A NAME="RD29508ST-16E">16e</A>
Shaabani A.
Maleki A.
Chem. Pharm. Bull.
2008,
56:
79
<A NAME="RD29508ST-17A">17a</A>
Singh SK.
Gupta P.
Duggineni S.
Kundu B.
Synlett
2003,
2147
<A NAME="RD29508ST-17B">17b</A>
Das B.
Venkateswarlu K.
Suneel K.
Majhi A.
Tetrahedron Lett.
2007,
48:
5371
<A NAME="RD29508ST-18">18</A>
Cho CS.
Oh SG.
Tetrahedron Lett.
2006,
47:
5633
<A NAME="RD29508ST-19A">19a</A>
Antoniotti S.
Duñach E.
Tetrahedron
Lett.
2002,
43:
3971
<A NAME="RD29508ST-19B">19b</A>
Nasar MK.
Kumar RR.
Perumal S.
Tetrahedron Lett.
2007,
48:
2155
<A NAME="RD29508ST-20">20</A>
Cho CS.
Ren WX.
Shim SC.
Tetrahedron
Lett.
2007,
48:
4665
<A NAME="RD29508ST-21">21</A>
Krasavin M.
Parchinsky V.
Synlett
2008,
645
<A NAME="RD29508ST-22A">22a</A>
Dömling A.
Ugi I.
Angew.
Chem. Int. Ed.
2000,
39:
3168
<A NAME="RD29508ST-22B">22b</A>
Dömling A.
Chem. Rev.
2006,
106:
17
<A NAME="RD29508ST-22C">22c</A>
Tietze LF.
Chem. Rev.
1996,
96:
115
<A NAME="RD29508ST-22D">22d</A>
Posner
GH.
Chem. Rev.
1986,
86:
831
<A NAME="RD29508ST-22E">22e</A>
Ramón DJ.
Yus M.
Angew.
Chem. Int. Ed.
2005,
44:
1602
<A NAME="RD29508ST-23">23</A>
Bienaymé H.
Hulme C.
Oddon G.
Schmitt P.
Chem. Eur. J.
2000,
6:
3321
<A NAME="RD29508ST-24A">24a</A>
Van Leusen D.
Van Leusen AM.
Org.
React.
2001,
57:
417
<A NAME="RD29508ST-24B">24b</A>
Tandon VK.
Rai S.
Sulfur Reports
2003,
24:
307
<A NAME="RD29508ST-25A">25a</A>
Denmark SE.
Fan Y.
J.
Org. Chem.
2005,
70:
9667
<A NAME="RD29508ST-25B">25b</A>
Krishna PR.
Dayaker G.
Reddy PVN.
Tetrahedron Lett.
2006,
47:
5977
<A NAME="RD29508ST-26A">26a</A>
Sisko J.
Kassick AJ.
Mellinger M.
Filan JJ.
Allen A.
Olsen MA.
J.
Org. Chem.
2000,
65:
1516
<A NAME="RD29508ST-26B">26b</A>
Ten-Have R.
Huisman M.
Meetsma A.
Van Leusen AM.
Tetrahedron
1997,
33:
11355
<A NAME="RD29508ST-26C">26c</A>
Beck B.
Leppert CA.
Mueller BK.
Dömling A.
QSAR
Com. Sci.
2006,
25:
527
<A NAME="RD29508ST-27">27</A>
Terzidis M.
Tsoleridis CA.
Stephanidou-Stephanatou J.
Tetrahedron
2007,
63:
7828
<A NAME="RD29508ST-28">28</A>
Evolution of gas with alkaline pH
and characteristic amine odor was detected.
<A NAME="RD29508ST-29">29</A>
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.
<A NAME="RD29508ST-30">30</A>
Higashino T.
Takemoto M.
Tanji K.-I.
Iijima C.
Hayashi E.
Chem.
Pharm. Bull.
1985,
33:
4193
<A NAME="RD29508ST-31">31</A>
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.
