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
1
Ugi I.
Angew.
Chem., Int. Ed. Engl.
1982,
21:
810
2
Dömling A.
Chem.
Rev.
2006,
106:
17
3
Dömling A.
Ugi I.
Angew. Chem. Int. Ed.
2000,
39:
3168
4
Ahmadi E.
Ramazani A.
Haghighi M. N.
Tetrahedron Lett.
2007,
48:
6954
5
Zinner G.
Moderhack D.
Kliegel W.
Chem.
Ber.
1969,
102:
2536
6a
Nair V.
Nair JS.
Vinod AU.
Rath NP.
J.
Chem. Soc., Perkin Trans. 1
1997,
3129
6b
Nair V.
Nair JS.
Vinod AU.
Synthesis
2000,
1713
6c
Nair V.
Bindu S.
Balgopal L.
Tetrahedron
Lett.
2001,
42:
2043
6d
Nair V.
Vinod AU.
Chem. Commun.
2000,
1019
7
Yadav JS.
Reddy SBV.
Shubashree S.
Shadiv K.
Naidu JJ.
Synthesis
2004,
2376
8a
Nair V.
Vinod AU.
J.
Org. Chem.
2001,
66:
4427
8b
Nair V.
Vinod AU.
Nair JS.
Sreekanth AR.
Rath NP.
Tetrahedron Lett.
2000,
41:
6675
8c
Nair V.
Vinod AU.
Ramesh R.
Menon RS.
Varma RL.
Mathew S.
Chiaroni A.
Heterocycles
2002,
58:
147
8d
Nair V.
Mathen JS.
Vinod AU.
Varma RL.
Chem.
Lett.
2001,
30:
738
9a
Yavari I.
Adib M.
Sayahi MH.
J. Chem. Soc., Perkin Trans. 1
2002,
2343
9b
Yavari I.
Nasiri F.
Moradi L.
Djahaniani H.
Tetrahedron Lett.
2004,
45:
7099
10
Winterfeldt E.
Schumann D.
Dillinger HJ.
Chem.
Ber.
1969,
102:
1656
11
Adib M.
Koloogani SA.
Abbasi A.
Bijanzadeh HR.
Synthesis
2007,
3056
12 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.
13
Adib M.
Sayahi MH.
Rahbari S.
Tetrahedron
Lett.
2005,
46:
6545
14
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
15 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
Hosseini-Sarvari M.
Sharghi H.
J.
Org. Chem.
2006,
71:
6652
16b
Janza B.
Studer A.
Org. Lett.
2006,
8:
1875
17a
Taylor EC.
Haley NF.
Clemens RJ.
J.
Am. Chem. Soc.
1981,
103:
7743
17b
Perri ST.
Slater SC.
Toske
SG.
White JD.
J.
Org. Chem.
1990,
55:
6037
17c
Shintani R.
Fu GC.
J. Am. Chem. Soc.
2003,
125:
10778
17d
Suárez A.
Downey CW.
Fu GC.
J. Am. Chem. Soc.
2005,
127:
11244
17e
Shintani R.
Hayashi T.
J. Am. Chem. Soc.
2006,
128:
6330
17f
Sibi MP.
Stanley LM.
Nie X.
Venkatraman L.
Liu M.
Jasperse CP.
J. Am.
Chem. Soc.
2007,
129:
395