Abstract
The 1,3-dipolar cycloaddition of azomethine ylides is a versatile and efficient tool for the construction of five-membered nitrogen heterocycles. When the azomethine ylide is conjugated with double bonds other pericyclic pathways become available, including 1,5- or 1,7-electrocyclizations, with the latter 8π-electron process having only recently emerged as a potentially useful method for the formation of seven-membered heterocycles. Under special structural circumstances, multistep rearrangements can also be observed. In this account, a summary of our work on the exploration and development of 1,7-electrocyclizations of azomethine ylides is presented.
1 Introduction
2 Electrocyclizations
2.1 Reaction of β-Phenylcinnamaldehyde with Amino Acids: The First 1,7-Electrocyclization of Nonstabilized Azomethine Ylides
2.2 Synthesis of Azepines from Unsaturated Aldehydes and Sarcosine via 1,7-Electrocyclizations
2.3 Electrocyclizations of Stabilized Azomethine Ylides
2.4 Electrocyclizations of Azomethine Ylides onto a N=O Double Bond
3 Conclusions
Key words
azomethine ylides - electrocyclization - heterocycles
References 1 Current address: Servier Research Institute of Medicinal Chemistry, 1131 Budapest Záhony u. 7, Hungary.
2a Pandey G.
Banerjee P.
Gadre SR.
Chem. Rev.
2006,
106:
4484
2b Coldham I.
Hufton R.
Chem. Rev.
2005,
105:
2765
2c Husinec S.
Savic V.
Tetrahedron: Asymmetry
2005,
16:
2047
2d Najera C.
Sansano JM.
Curr. Org. Chem.
2003,
7:
1105
2e Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products
Padwa A.
Pearson WH.
Wiley;
New York:
2002.
2f Tsuge O.
Kanemasa S.
Adv. Heterocycl. Chem.
1989,
45:
232
2g Grigg R.
Chem. Soc. Rev.
1987,
16:
89
3 Woodward RB.
Hoffmann R.
Angew. Chem., Int. Ed. Engl.
1969,
8:
781
4 Bates RB.
Deines WH.
McCombs DA.
Potter DE.
J. Am. Chem. Soc.
1969,
91:
4608
5a Taylor EC.
Turchi IJ.
Chem. Rev.
1979,
79:
181
5b Huisgen R.
Angew. Chem., Int. Ed. Engl.
1980,
19:
947
5c Zecchi G.
Synthesis
1991,
181
5d Groundwater PW.
Nyerges M.
Adv. Heterocycl. Chem.
1999,
73:
97
5e Pinho e Melo TMVD.
Eur. J. Org. Chem.
2006,
2873
6a Mayer T.
Maas G.
Tetrahedron Lett.
1992,
33:
205
6b Reinhard R.
Glaser M.
Neumann R.
Maas G.
J. Org. Chem.
1997,
62:
7744
7a Klop W.
Brandsma L.
J. Chem. Soc., Chem. Commun.
1983,
988
7b Dhimane H.
Pommelet JC.
Chuche J.
Lhommet G.
Richaud WG.
Haddad M.
Tetrahedron Lett.
1985,
26:
833
7c McNab H.
Monahan LC.
Gray T.
J. Chem. Soc., Chem. Commun.
1987,
140
8a Maier W.
Eberbach W.
Fritz H.
Helv. Chim. Acta
1991,
74:
1095
8b Marx K.
Eberbach W.
Tetrahedron
1997,
53:
14687
9a Groundwater PW.
Sharif T.
Arany A.
Hibbs DE.
Hurthouse MB.
Nyerges M.
Tetrahedron Lett.
1998,
39:
1433
9b Groundwater PW.
Sharif T.
Arany A.
Hibbs DE.
Hurthouse MB.
Garnett I.
Nyerges M.
J. Chem. Soc., Perkin Trans. 1
1998,
2837
10 Nyerges M.
Arany A.
Fejes I.
Groundwater PW.
Zhang W.
Bendell D.
Anderson RJ.
Töke L.
Tetrahedron
2002,
58:
989
11a Rizzi GR.
J. Org. Chem.
1970,
35:
2069
11b Grigg R.
Thianpatanagul S.
J. Chem. Soc., Chem. Commun.
1984,
180
11c Joucla M.
Mortier J.
J. Chem. Soc., Chem. Commun.
1985,
1566
11d Tsuge O.
Kanemasa S.
Ohe M.
Takenaka S.
Bull. Chem. Soc. Jpn.
1987,
60:
4079
11e Nyerges M.
Balázs L.
Bitter I.
Kádas I.
Kövesdi I.
Töke L.
Tetrahedron
1995,
51:
6783
12 Arany A.
Groundwater PW.
Nyerges M.
Tetrahedron Lett.
1998,
39:
3267
13 Zhang W.
PhD Thesis
University of Sunderland;
UK:
2001.
14 Arany A.
Bendell D.
Groundwater PW.
Garnett I.
Nyerges M.
J. Chem. Soc., Perkin Trans. 1
1999,
2605
15 Nyerges M.
Pintér .
Virányi A.
Bitter I.
Töke L.
Tetrahedron Lett.
2005,
46:
377
16a Pintér .
Nyerges M.
Virányi A.
Töke L.
Tetrahedron Lett.
2003,
44:
2343
16b Nyerges M.
Pintér .
Virányi A.
Blaskó G.
Töke L.
Tetrahedron
2005,
61:
8199
17a Nyerges M.
Virányi A.
Pintér .
Töke L.
Tetrahedron Lett.
2003,
44:
793
17b Tóth J.
Dancsó A.
Blaskó G.
Töke L.
Groundwater PW.
Nyerges M.
Tetrahedron
2006,
62:
5725
18 Nyerges M.
Virányi A.
Tóth J.
Blaskó G.
Töke L.
Synthesis
2006,
1273
19 Grigg R.
Kennewell P.
Savic V.
Sridharan V.
Tetrahedron
1992,
48:
10423
20 Tóth J.
Nedves A.
Blaskó G.
Dancsó A.
Töke L.
Nyerges M.
Synthesis
2007,
1003
21 Nyerges M.
Töke L.
Tetrahedron Lett.
2005,
46:
7531
22a Doyle MP.
Hu W.
Timmons DJ.
Org. Lett.
2001,
3:
3741
22b Doyle MP.
Yan M.
Hu W.
Gronenberg LS.
J. Am. Chem. Soc.
2003,
125:
4692
23 Tan Y.
Hartmann T.
Huch V.
Dürr H.
Valat P.
Wintgens V.
Kossanyi J.
J. Org. Chem.
2001,
66:
1130
24 Tan Y.
Ahmed AS.
Dürr H.
Huch V.
Abdel-Wahab A.
Chem. Commun.
2001,
1246
25 Friebolin W.
Eberbach W.
Tetrahedron
2001,
57:
4349
26 Kusama H.
Suzuki Y.
Takaya J.
Iwasawa N.
Org. Lett.
2006,
8:
895
27 Nyerges M.
Heterocycles
2004,
63:
1685
28 Nyerges M.
Fejes I.
Virányi A.
Groundwater PW.
Töke L.
Tetrahedron Lett.
2001,
42:
5081
29 Tóth J.
Blaskó G.
Dancsó A.
Töke L.
Nyerges M.
Synth. Commun.
2006,
36:
3581
30 Nyerges M.
Fejes I.
Virányi A.
Groundwater PW.
Töke L.
Synthesis
2001,
1479
31 Nyerges M.
Virányi A.
Zhang W.
Groundwater PW.
Blaskó G.
Töke L.
Tetrahedron
2004,
60:
9937
32 Grashey R.
Angew. Chem., Int. Ed. Engl.
1962,
1:
158
33 Nyerges M.
Somfai B.
Tóth J.
Dancsó A.
Blaskó G.
Töke L.
Synthesis
2005,
2039
34 Kouznetsov V.
Palma A.
Ewert C.
Curr. Org. Chem.
2001,
5:
519
