Abstract
It was found that the zwitterionic intermediate obtained from
the addition of isocyanides to dimethyl acetylenedicarboxylate could
react with 1,3-dipolar compounds under mild conditions to produce
5-imino-2,3,5,8-tetrahydropyrazolo[1,2-a ]pyridazin-1-one derivatives
in high yields. A plausible mechanism was also discussed for this
process.
Key words
isocyanide - dimethyl acetylenedicarboxylate - multicomponent
reactions - 1,3-dipolar compounds - 5-imino-2,3,5,8-tetrahydropyrazolo[1,2-a ]pyridazin-1-one
References
<A NAME="RF22408SS-1">1 </A>
Ugi I.
Angew.
Chem., Int. Ed. Engl.
1982,
21:
810
<A NAME="RF22408SS-2">2 </A>
Dömling A.
Chem.
Rev.
2006,
106:
17
<A NAME="RF22408SS-3">3 </A>
Dömling A.
Ugi I.
Angew. Chem. Int. Ed.
2000,
39:
3168
<A NAME="RF22408SS-4">4 </A>
Ahmadi E.
Ramazani A.
Haghighi M. N.
Tetrahedron Lett.
2007,
48:
6954
<A NAME="RF22408SS-5">5 </A>
Zinner G.
Moderhack D.
Kliegel W.
Chem.
Ber.
1969,
102:
2536
6a </A>
Nair V.
Nair JS.
Vinod AU.
Rath NP.
J.
Chem. Soc., Perkin Trans. 1
1997,
3129
6b </A>
Nair V.
Nair JS.
Vinod AU.
Synthesis
2000,
1713
6c </A>
Nair V.
Bindu S.
Balgopal L.
Tetrahedron
Lett.
2001,
42:
2043
6d </A>
Nair V.
Vinod AU.
Chem. Commun.
2000,
1019
<A NAME="RF22408SS-7">7 </A>
Yadav JS.
Reddy SBV.
Shubashree S.
Shadiv K.
Naidu JJ.
Synthesis
2004,
2376
8a </A>
Nair V.
Vinod AU.
J.
Org. Chem.
2001,
66:
4427
8b </A>
Nair V.
Vinod AU.
Nair JS.
Sreekanth AR.
Rath NP.
Tetrahedron Lett.
2000,
41:
6675
8c </A>
Nair V.
Vinod AU.
Ramesh R.
Menon RS.
Varma RL.
Mathew S.
Chiaroni A.
Heterocycles
2002,
58:
147
8d </A>
Nair V.
Mathen JS.
Vinod AU.
Varma RL.
Chem.
Lett.
2001,
30:
738
9a </A>
Yavari I.
Adib M.
Sayahi MH.
J. Chem. Soc., Perkin Trans. 1
2002,
2343
9b </A>
Yavari I.
Nasiri F.
Moradi L.
Djahaniani H.
Tetrahedron Lett.
2004,
45:
7099
<A NAME="RF22408SS-10">10 </A>
Winterfeldt E.
Schumann D.
Dillinger HJ.
Chem.
Ber.
1969,
102:
1656
<A NAME="RF22408SS-11">11 </A>
Adib M.
Koloogani SA.
Abbasi A.
Bijanzadeh HR.
Synthesis
2007,
3056
<A NAME="RF22408SS-12">12 </A>
The atomic coordinates for 4a have been deposited at the Cambridge
Crystallographic Data Centre (deposition number CCDC 702357). The
coordinates can be obtained on request from the Director Cambridge
Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ,
UK, e-mail: deposit@ccdc.cam.ac.uk, fax: +44(1223)336033.
<A NAME="RF22408SS-13">13 </A>
Adib M.
Sayahi MH.
Rahbari S.
Tetrahedron
Lett.
2005,
46:
6545
<A NAME="RF22408SS-14">14 </A>
Walborsky HM.
Periasamy MP. In The Chemistry of Functional Groups , Supplement C
Patai S.
Rappaport Z.
Wiley;
New
York:
1983.
Chap. 20.
p.835-837
<A NAME="RF22408SS-15">15 </A>
The atomic coordinates for 8 have been deposited at the Cambridge
Crystallographic Data Centre (deposition number CCDC 713140). The
coordinates can be obtained on request from the Director Cambridge
Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ,
UK, e-mail: deposit@ccdc.cam.ac.uk, fax: +44(1223)336033.
16a </A>
Hosseini-Sarvari M.
Sharghi H.
J.
Org. Chem.
2006,
71:
6652
16b </A>
Janza B.
Studer A.
Org. Lett.
2006,
8:
1875
17a </A>
Taylor EC.
Haley NF.
Clemens RJ.
J.
Am. Chem. Soc.
1981,
103:
7743
17b </A>
Perri ST.
Slater SC.
Toske
SG.
White JD.
J.
Org. Chem.
1990,
55:
6037
17c </A>
Shintani R.
Fu GC.
J. Am. Chem. Soc.
2003,
125:
10778
17d </A>
Suárez A.
Downey CW.
Fu GC.
J. Am. Chem. Soc.
2005,
127:
11244
17e </A>
Shintani R.
Hayashi T.
J. Am. Chem. Soc.
2006,
128:
6330
17f </A>
Sibi MP.
Stanley LM.
Nie X.
Venkatraman L.
Liu M.
Jasperse CP.
J. Am.
Chem. Soc.
2007,
129:
395
