Abstract
Different aldehydes and amines react with acyl cyanides in the presence of a catalytic
amount of the Schreiner thiourea catalyst to give the corresponding N -acyl amino nitriles in high yields. The scope of the reaction is broad and both aromatic
and aliphatic aldehydes and amines can readily be used.
Key words
acylcyanation - α-amino nitriles - multicomponent reactions - organocatalysis - acyl
cyanides
References and Notes
<A NAME="RG31706ST-1">1 </A>
Strecker A.
Ann. Chem. Pharm.
1850,
75:
27
For reviews, see:
<A NAME="RG31706ST-2A">2a </A>
Gröger H.
Chem. Rev.
2003,
103:
2795
<A NAME="RG31706ST-2B">2b </A>
Yet L.
Angew. Chem. Int. Ed.
2001,
40:
875
<A NAME="RG31706ST-2C">2c </A>
Spino C.
Angew. Chem. Int. Ed.
2004,
43:
1764
<A NAME="RG31706ST-2D">2d </A>
Enders D.
Shilvock JP.
Chem. Soc. Rev.
2000,
29:
359
For reviews on multicomponent reactions, see:
<A NAME="RG31706ST-3A">3a </A>
Ugi I.
Dömling A.
Ebert B.
Comb. Chem. High Throughput Screening
1999,
125
<A NAME="RG31706ST-3B">3b </A>
Ugi I.
Pure Appl. Chem.
2001,
73:
187
<A NAME="RG31706ST-3C">3c </A>
Dömling A.
Ugi I.
Angew. Chem. Int. Ed.
2000,
39:
3168
<A NAME="RG31706ST-3D">3d </A>
Ramón DJ.
Yus M.
Angew. Chem. Int. Ed.
2005,
44:
1602
<A NAME="RG31706ST-4A">4a </A>
Tian J.
Yamagiwa N.
Matsunaga S.
Shibasaki M.
Angew. Chem. Int. Ed.
2002,
41:
3636
<A NAME="RG31706ST-4B">4b </A>
Tian J.
Yamagiwa N.
Matsunaga S.
Shibasaki M.
Org. Lett.
2003,
5:
3021
<A NAME="RG31706ST-4C">4c </A>
Yamagiwa N.
Tian J.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2005,
127:
3413
<A NAME="RG31706ST-4D">4d </A>
Tian S.-K.
Deng L.
J. Am. Chem. Soc.
2001,
123:
6295
<A NAME="RG31706ST-4E">4e </A>
Casas J.
Baeza A.
Sansano JM.
Nájera C.
Saá JM.
Tetrahedron: Asymmetry
2003,
14:
197
<A NAME="RG31706ST-4F">4f </A>
Belokon YN.
Blacker AJ.
Clutterbuck LA.
North M.
Org. Lett.
2003,
5:
4505
<A NAME="RG31706ST-4G">4g </A>
Lundgren S.
Wingstrand E.
Penhoat M.
Moberg C.
J. Am. Chem. Soc.
2005,
127:
11592
<A NAME="RG31706ST-4H">4h </A>
Belokon YN.
Ishibashi E.
Nombra H.
North M.
Chem. Commun.
2006,
16:
1775
<A NAME="RG31706ST-5A">5a </A>
Hoffmann S.
Seayad AM.
List B.
Angew. Chem. Int. Ed.
2005,
44:
7424
<A NAME="RG31706ST-5B">5b </A>
Seayad J.
Seayad AM.
List B.
J. Am. Chem. Soc.
2006,
128:
1086
<A NAME="RG31706ST-5C">5c </A>
Hoffmann S.
Nicoletti M.
List B.
J. Am. Chem. Soc.
2006,
128:
13074
<A NAME="RG31706ST-6">6 </A>
Pan SC.
Zhou J.
List B.
Synlett
2006,
3275
For reviews, see:
<A NAME="RG31706ST-7A">7a </A>
Schreiner PR.
Chem. Soc. Rev.
2003,
32:
289
<A NAME="RG31706ST-7B">7b </A>
Seayad J.
List B.
Org. Biomol. Chem.
2005,
3:
719
<A NAME="RG31706ST-7C">7c </A>
Taylor MS.
Jacobsen EN.
Angew. Chem. Int. Ed.
2006,
45:
1520
<A NAME="RG31706ST-7D">7d </A>
Connon SJ.
Chem. Eur. J.
2006,
12:
5418
<A NAME="RG31706ST-7E">7e </A>
Pihko PM.
Angew. Chem. Int. Ed.
2004,
43:
2062
<A NAME="RG31706ST-7F">7f </A>
Connon SJ.
Angew. Chem. Int. Ed.
2006,
45:
3909
<A NAME="RG31706ST-7G">7g </A>
Akiyama T.
Itoh J.
Fuchibe K.
Adv. Synth. Catal.
2006,
348:
999
<A NAME="RG31706ST-8A">8a </A>
Schreiner PR.
Wittkopp A.
Org. Lett.
2002,
4:
217
<A NAME="RG31706ST-8B">8b </A>
Wittkopp A.
Schreiner PR.
Chem. Eur. J.
2003,
9:
407
<A NAME="RG31706ST-9A">9a </A>
Dornow A.
Lüpfert S.
Chem. Ber.
1956,
89:
2718
<A NAME="RG31706ST-9B">9b </A>
Dornow A.
Lüpfert S.
Chem. Ber.
1957,
90:
1780
<A NAME="RG31706ST-9C">9c </A>
Dornow A, and
Lüpfert S. inventors; US 2849477.
<A NAME="RG31706ST-9D">9d </A>
Gardent MJ.
Delépine MM.
C. R. Acad. Sci.
1958,
247:
2153
<A NAME="RG31706ST-9E">9e </A>
Rai M.
Krishan K.
Singh A.
Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.
1978,
16:
834
<A NAME="RG31706ST-9F">9f </A>
Sakamoto M.
Akiyama Y.
Furumi N.
Ishii K.
Tomimatsu Y.
Date T.
Chem. Pharm. Bull.
1983,
31:
2623
<A NAME="RG31706ST-10">10 </A>
On mixing aldehyde, amine, catalyst, additive, and acetyl cyanide together at 0 °C,
the product was obtained with poor yield due to considerable side product formation.