Novel One-Pot Synthesis of 2-Substituted 3-Alkoxyisoindolin-1-imine Deri­vatives from 2-Cyanobenzaldehyde, Amine, and Alcohol

Abstract

A novel, one-pot procedure has been developed for the synthesis of 2-substituted 3-alkoxyisoindolin-1-imine derivatives via three-component condensation of 2-cyanobenzaldehyde, amine, and alcohol. The efficient and convenient reaction conditions provide the corresponding products from various substrates in good yields (65–96%) catalyzed by acetic acid. The straightforward procedure is a valid contribution to methods for the synthesis of isoindolin-1-imine derivatives.

Key words

2-cyanobenzaldehyde - isoindolin-1-imine - multicomponent reaction - 3-alkoxyisoindolin-1-imine

• References

• 1a Jiaang W, Chen Y, Hsu T, Wu S, Chien C, Chang C, Chang S, Lee S, Chen X. Bioorg. Med. Chem. Lett. 2005; 15: 687
• 1b Müller A, Höfner G, Renukappa-Gutke T, Parsons CG, Wanner KT. Bioorg. Med. Chem. Lett. 2011; 21: 5795
• 1c Norman MH, Minick DJ, Rigdon GC. J. Med. Chem. 1996; 39: 149
• 1d Luo W, Yu Q, Salcedo I, Holloway HW, Lahiri DK, Brossi A, Tweedie D, Greig NH. Bioorg. Med. Chem. 2011; 19: 3965
• 2a Kundu NG, Khan MW. Tetrahedron 2000; 56: 4777
• 2b Botero Cid HM, Tränkle C, Baumann K, Pick R, Mies-Klomfass E, Kostenis E, Mohr K, Holzgrabe U. J. Med. Chem. 2000; 43: 2155
• 2c Holzgrabe U, Bender W, Botero Cid HM, Staudt M, Pick R, Pfletschinger C, Balatková E, Tränkle C, Mohr K. Pharm. Acta Helv. 2000; 74: 149
• 3 Nguyen KT, Claiborne CF, McCauley JA, Libby BE, Claremon DA, Bednar RA, Mosser SD, Gaul SL, Connolly TM, Condra CL, Bednar B, Stump GL, Lynch JJ, Koblan KS, Liverton NJ. Bioorg. Med. Chem. Lett. 2007; 17: 3997
• 4a Zhang H, Maryanoff B, White K, Yabut SC, Ye H, Chen C. US 20110105490, 2011 ; Chem. Abstr. 2011, 154, 557419.
• 4b Clark R, Takemura A, Watanabe N, Asano O, Nagakura T, Tabata K. US 20090270433, 2009 ; Chem. Abstr. 2009, 150, 352175.
• 5 Sović I, Stilinović V, Kaitner B, Kraljević-Pavelić S, Bujak M, Cujak K, Novak P, Karminski-Zamola G. J. Mol. Struct. 2011; 1006: 259
• 6a Shimomura N, Sasho M, Kayono A, Kazuhiro Y, Masahiko T, Kuroda H, Furukawa K. US 7375236, 2008 ; Chem. Abstr. 2008, 144, 311793.
• 6b Sato R, Nakayama M, Yuzawa Y, Goto T, Saito M. Chem. Lett. 1985; 1887
• 6c Luo W, Yu Q, Salcedo I, Holloway HW, Tweedie D, Greig NH, Lahiri DK, Brossi A. Bioorg. Med. Chem. 2011; 19: 3965
• 6d Nan’ya S, Tange T, Maekawa E. J. Heterocycl. Chem. 1985; 22: 449
• 7a Xiao Z, Lei M, Hu L. Tetrahedron Lett. 2011; 52: 7099
• 7b Liu J, Lei M, Hu L. Green Chem. 2012; 14: 840
• 7c Lei M, Ma L, Hu L. Tetrahedron Lett. 2009; 50: 6393
• 7d Lei M, Ma L, Hu L. Tetrahedron Lett. 2010; 51: 4746