A Convenient Metal-Free Synthesis of (E)-3-Styrylisocoumarins through Annulation of (E)-1,4-Diarylenynes

This manuscript is dedicated to the memory of Professor Jean-François Normant

Abstract

A metal-free procedure for the cyclization of (E)-1,4-di­arylenynes is described. The reaction is promoted by a catalytic amount of p-toluenesulfonic acid and takes place in ethanol at 160 °C under microwave irradiation to afford stereoselectively (E)-3-styrylisocoumarins in good to excellent yields.

Key words

styrylisocoumarins - cyclization - enynes - p-toluenesulfonic acid - Suzuki couplings

• References

• 1 Pal S, Chatare V, Pal M. Curr. Org. Chem. 2011; 15: 782
• 2a Mizuno M, Yoshida S, Iinuma M, Tanaka T, Lang FA, Goto K. Chem. Pharm. Bull. 1990; 38: 2075
• 2b Saeed A, Rafique H, Ashraf Z. J. Asian Nat. Prod. Res. 2013; 15: 130
• 2c Iinuma M, Tosa H, Tanaka T, Mizuno M, Lang FA. J. Nat. Prod. 1993; 56: 1638
• 2d Rama NH, Iqbal R, Zamani K, Saeed A, Hussain MT. J. Chem. Soc. Pak. 2000; 22: 130
• 3 Napolitano E. Org. Prep. Proced. Int. 1997; 29: 631
• 4 Saeed A, Mahesar PA. Tetrahedron 2014; 70: 1401
• 5 Saeed A, Rama NH, Arfan M. J. Heterocycl. Chem. 2003; 40: 519
• 6 Kale AP, Pawar GG, Kapur M. Org. Lett. 2012; 14: 1808
• 7a Tréguier B, Rasolofonjatovo E, Hamze A, Provot O, Bignon J, Dubois J, Brion J.-D, Alami M. Eur. J. Org. Chem. 2011; 4868
• 7b Lawson M, Hamze A, Peyrat J.-F, Bignon J, Dubois J, Brion J.-D, Alami M. Org. Biomol. Chem. 2013; 11: 3664
• 8a Jacubert M, Hamze A, Provot O, Peyrat J.-F, Brion J.-D, Alami M. Tetrahedron Lett. 2009; 50: 3588
• 8b Jacubert M, Provot O, Peyrat J.-F, Hamze A, Brion J.-D, Alami M. Tetrahedron 2010; 66: 3775
• 8c Mousset C, Provot O, Hamze A, Bignon J, Brion J.-D, Alami M. Tetrahedron 2008; 64: 4287
• 8d Treguier B, Rasolofonjatovo E, Hamze A, Provot O, Wdzieczak-Bakala J, Dubois J, Brion J.-D, Alami M. Eur. J. Org. Chem. 2011; 4868
• 8e Rasolofonjatovo E, Treguier B, Provot O, Hamze A, Morvan E, Brion J.-D, Alami M. Tetrahedron Lett. 2011; 52: 1036
• 8f Rasolofonjatovo E, Treguier B, Provot O, Hamze A, Brion J.-D, Alami M. Eur. J. Org. Chem. 2012; 1603
• 8g Rasolofonjatovo E, Provot O, Hamze A, Rodrigo J, Bignon J, Wdzieczak-Bakala J, Lenoir C, Desravines D, Dubois J, Brion J.-D, Alami M. Eur. J. Med. Chem. 2013; 62: 28
• 8h Renko D, Provot O, Rasolofonjatovo E, Bignon J, Rodrigo J, Dubois J, Brion J.-D, Hamze A, Alami M. Eur. J. Med. Chem. 2015; 90: 834
• 9 Le Bras G, Hamze A, Messaoudi S, Provot O, Le Calvez PB, Brion J.-D, Alami M. Synthesis 2008; 1607
• 10a Alami M, Gueugnot S, Domingues E, Linstrumelle G. Tetrahedron 1995; 51: 1209
• 10b Alami M, Peyrat J.-F, Brion J.-D. Synthesis 2000; 1499
• 11 Tikad A, Hamze A, Provot O, Brion J.-D, Alami M. Eur. J. Org. Chem. 2010; 725
• 12 Baldwin JE. J. Chem. Soc., Chem. Commun. 1976; 734
• 13 Littke AF, Dai C, Fu GC. J. Am. Chem. Soc. 2000; 122: 4020
• 14 Penthala NR, Thakkar S, Crooks PA. Bioorg. Med. Chem. Lett. 2015; 25: 2763