CC BY-ND-NC 4.0 · SynOpen 2018; 02(04): 0298-0305
DOI: 10.1055/s-0037-1610399
paper
Copyright with the author

Efficient One-Pot Synthesis of Triazole-Linked Morpholinone Scaffolds by CuAAC in the Presence of 18-Crown-6

A. Mayooufi
a   Laboratoire Synthèse et Isolement de Molécules BioActives (SIMBA), EA7502, Université de Tours, Faculté des Sciences et Techniques, Parc de Grandmont, 32 av. Monge, 37200 Tours, France   Email: jerome.thibonnet@univ-tours.fr
b   Laboratoire de Chimie Organique Structurale et Macromoléculaire, Département de Chimie, Faculté des Sciences de Tunis, Campus Universitaire El-Manar, Rue Béchir Salem Belkheiria, 2092 Tunis, Tunisie
,
M. Romdhani-Younes
b   Laboratoire de Chimie Organique Structurale et Macromoléculaire, Département de Chimie, Faculté des Sciences de Tunis, Campus Universitaire El-Manar, Rue Béchir Salem Belkheiria, 2092 Tunis, Tunisie
,
J. Thibonnet*
a   Laboratoire Synthèse et Isolement de Molécules BioActives (SIMBA), EA7502, Université de Tours, Faculté des Sciences et Techniques, Parc de Grandmont, 32 av. Monge, 37200 Tours, France   Email: jerome.thibonnet@univ-tours.fr
› Author Affiliations
Further Information

Publication History

Received: 08 October 2018

Accepted after revision: 02 November 2018

Publication Date:
22 November 2018 (online)


Abstract

A range of bis-heterocyclic derivatives based on novel morpholinone­ and triazole heterocycles was prepared from iodo-morpholinone­. The key step in our strategy is a one-pot procedure based upon copper-catalysed alkyne-azide cycloaddition (CuAAC) from iodo-morpholinone.

Supporting Information

 
  • References

  • 1 Agarwal R, Ansari MH, Khan MW. Y, Ahmad M, Sharma KD. J. Am. Oil Chem. Soc. 1989; 66: 825
  • 2 Gonzalez AZ, Eksterowicz J, Bartberger MD, Beck HP, Canon J, Chen A, Chow D, Duquette J, Fox BM, Fu J, Huang X, Houze JB, Jin L, Li Y, Li Z, Ling Y, Lo M.-C, Long AM, McGee LR, McIntosh J, McMinn DL, Oliner JD, Osgood T, Rew Y, Saiki AY, Shaffer P, Wortman S, Yakowec P, Yan X, Ye Q, Yu D, Zhao X, Zhou J, Olson SH, Medina JC, Sun D. J. Med. Chem. 2014; 57: 2472
  • 3 Duang Y.-C, Ma Y.-C, Zhang E, Shi X.-J, Wang M.-M, Ye X.-W, Liu H.-M. Eur. J. Med. Chem. 2013; 62: 11
  • 4 Haider S, Alam MS, Hamid H, Shafi S, Nargotra A, Mahajan P, Nazreen S, Kalle AM, Kharbanda C, Ali Y, Alam A, Panda AK. Eur. J. Med. Chem. 2013; 70: 579
  • 5 Piotrowska DG, Balzarini J, Glowacka IE. Eur. J. Med. Chem. 2012; 47: 501
  • 6 Phillips OA, Udo EE, Abdel-Hamid ME, Varghese R. Eur. J. Med. Chem. 2009; 44: 3217
  • 7 Others applications: Chinthala Y, Domatti AK, Sarfaraz A, Singh SP, Arigari NK, Gupta N, Satya SK. V. N, Kumar JK, Khan F, Tiwari AK, Paramjit G. Eur. J. Med. Chem. 2013; 70: 308
  • 8 Delaye P.-O, Petrignet J, Thiery E, Thibonnet J. Org. Biomol. Chem. 2017; 15: 7290
  • 9 Poornachandran M, Raghunathan R. Tetrahedron 2008; 64: 6461
  • 10 Yeom C.-E, Kim MJ, Kim BM. Tetrahedron 2007; 63: 904
    • 11a Cocker W. J. Chem. Soc. 1943; 373
    • 11b Olier C, Azzi N, Gil G, Gastaldi S, Bertrand MP. J. Org. Chem. 2008; 73: 8469
  • 12 Belmessieri D, Cordes DB, Slawin AM. Z, Smith AD. Org. Lett. 2013; 15: 3472
  • 13 Feula A, Dhillon SS, Byravan R, Sangha M, Ebanks R, Salih MA. H, Spencer N, Male L, Magyary I, Deng W.-P, Müller F, Fossey JS. Org. Biomol. Chem. 2013; 11: 5083
  • 14 Kumar S, Mujahid M, Verma AK. Org. Biomol. Chem. 2017; 15: 4686
  • 15 Liu H, Pan Y, Tan C.-H. Tetrahedron Lett. 2008; 49: 4424
  • 16 Liu H, Tan C.-H. Tetrahedron Lett. 2007; 48: 8220

    • For recent iodocyclizations, see:
    • 17a Grandclaudon C, Michelet V, Toullec PY. Synlett 2018; 310
    • 17b Zhou Y, Zhang X, Zhang Y, Ruan L, Zhang J, Zhang-Negrerie D, Du Y. Org. Lett. 2017; 19: 150
    • 17c Garcia-Garcia P, Sanjuan AM, Rashid MA, Martinez-Cuezva A, Fernandez-Rodriguez M, Rodriguez F, Sanz R. J. Org. Chem. 2017; 82: 1155
    • 17d Kamesu K, Krishnamohan GV, Rajasekhar K. Asian J. Chem. 2017; 29: 2704
    • 17e Sonawane AD, Garud DR, Udagawa T, Koketsu M. Org. Biomol. Chem. 2018; 16: 245
    • 18a Zhang X, Zhou Y, Wang H, Guo D, Ye D, Xu Y, Jiang H, Liu H. Adv. Synth. Catal. 2011; 353: 1429
    • 18b Alvarez-Corral M, Munoz-Dorado M, Rodriguez-Garcia I. Chem. Rev. 2008; 3174
  • 19 Heasley VL, Shellhamer DF, Heasley LE, Yaeger DB, Heasley GE. J. Org. Chem. 1980; 45: 4649
  • 20 Singh MS, Chowdhurry S. RCS Adv. 2012; 2: 4547
    • 21a Ugi I. Pure Appl. Chem. 2001; 73: 187; and references therein
    • 21b Multicomponent Reactions . Zhu J, Bienayme H. Wiley VCH; Weinheim, Germany: 2005
  • 23 Yi M, Gu P, Kang X.-Y, Sun J, Li R, Li X.-Q. Tetrahedron Lett. 2014; 55: 105
  • 24 Patonay T, Juhàsz-Toth E, Bènyei A. Eur. J. Org. Chem. 2002; 285
    • 25a Hassan S, Muller TJ. J. Adv. Synth. Catal. 2015; 357: 617
    • 25b Baltus CB, Jorda R, Marot C, Berk K, Bazgier V, Krystof V, Prié G, Viaud-Massuard MC. Eur. J. Org. Chem. 2016; 701
    • 25c Camp C, Dorbes S, Picard C, Benoist E. Tetrahedron Lett. 2008; 49: 1979
    • 25d Mishra KB, Tiwari VK. J. Org. Chem. 2014; 79: 5752
    • 25e Shamim A, Vasconcelos SN. S, De Oliveira IM, Reis JS, Pimenta DC, Zukerman-Schpector J, Stefani HA. Synthesis 2017; 5183
    • 25f Martinelli M, Milcent T, Ongeri S, Crousse B. Beilstein J. Org. Chem. 2008; 4: 19