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

A. Mayooufi; M. Romdhani-Younes; J. Thibonnet

doi:10.1055/s-0037-1610399

SynOpen, Table of Contents

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

^aLaboratoire 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

^bLaboratoire 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

^bLaboratoire 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*

^aLaboratoire 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

Abstract

All articles of this category

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.

Key words

click chemistry - iodolactonization - morpholinones - azides - 1,2,3-triazole - one-pot procedure

Full Text

References

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

22a Kumar D, Patel G, Reddy VB. Synlett 2009; 399
22b Alonso F, Moglie Y, Radivoy G, Yus M. Synlett 2012; 2179
22c Mukherjee N, Ahammed S, Bhadra S, Ranu BC. Green Chem. 2013; 15: 389
22d Feldman AK, Colasson B, Fokin VV. Org. Lett. 2004; 6: 3897
22e Safa KD, Mousazadeh H. Synth. Commun. 2016; 46: 1595
22f Guo S, Zhou Y, Dai B, Huo C, Liu C, Zhao Y. Synthesis 2018; 50: 2191

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

Supplementary Material

Supporting Information