Synthesis 2016; 48(19): 3382-3392
DOI: 10.1055/s-0035-1562501
paper
© Georg Thieme Verlag Stuttgart · New York

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

Guangkuan Zhao
BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France   Email: olivier.provot@u-psud.fr   Email: mouad.alami@u-psud.fr
,
Ling-Zhi Yuan
BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France   Email: olivier.provot@u-psud.fr   Email: mouad.alami@u-psud.fr
,
Mylène Roudier
BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France   Email: olivier.provot@u-psud.fr   Email: mouad.alami@u-psud.fr
,
Jean-François Peyrat
BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France   Email: olivier.provot@u-psud.fr   Email: mouad.alami@u-psud.fr
,
Abdallah Hamze
BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France   Email: olivier.provot@u-psud.fr   Email: mouad.alami@u-psud.fr
,
Jean-Daniel Brion
BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France   Email: olivier.provot@u-psud.fr   Email: mouad.alami@u-psud.fr
,
Olivier Provot*
BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France   Email: olivier.provot@u-psud.fr   Email: mouad.alami@u-psud.fr
,
Mouad Alami*
BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France   Email: olivier.provot@u-psud.fr   Email: mouad.alami@u-psud.fr
› Author Affiliations
Further Information

Publication History

Received: 17 May 2016

Accepted after revision: 30 May 2016

Publication Date:
04 July 2016 (online)


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.

Supporting Information

 
  • 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