Synthetic Approach Toward Heterocyclic Hybrids of [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines

Nawel Lechani; Maamar Hamdi; Baya Kheddis-Boutemeur; Oualid Talhi; Yacine Laichi; Khaldoun Bachari; Artur M. S. Silva

doi:10.1055/s-0036-1591991

Synlett, Table of Contents

Synlett 2018; 29(11): 1502-1504
DOI: 10.1055/s-0036-1591991

letter

Synthetic Approach Toward Heterocyclic Hybrids of [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines

Nawel Lechani

^aLaboratoire de Chimie Organique Appliquée, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediène BP 32, El-Alia Bab-Ezzouar, 16111 Alger, Algeria Email: prhamdi@gmail.com

^bDépartement de Chimie, Faculté des Sciences, Université Saad Dahleb, Blida, Algeria

,

Maamar Hamdi*

^aLaboratoire de Chimie Organique Appliquée, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediène BP 32, El-Alia Bab-Ezzouar, 16111 Alger, Algeria Email: prhamdi@gmail.com

,

Baya Kheddis-Boutemeur

^aLaboratoire de Chimie Organique Appliquée, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediène BP 32, El-Alia Bab-Ezzouar, 16111 Alger, Algeria Email: prhamdi@gmail.com

,

Oualid Talhi*

^cCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques, BP 384, Bou-Ismail, 42004 Tipaza, Algeria

^dQOPNA and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal Email: oualid.talhi@ua.pt Email: artur.silva@ua.pt

,

Yacine Laichi

^cCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques, BP 384, Bou-Ismail, 42004 Tipaza, Algeria

,

Khaldoun Bachari

^cCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques, BP 384, Bou-Ismail, 42004 Tipaza, Algeria

,

Artur M. S. Silva *

^dQOPNA and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal Email: oualid.talhi@ua.pt Email: artur.silva@ua.pt

› Author Affiliations

Abstract

All articles of this category

Abstract

The synthesis of novel heterocyclic [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine hybrids by a bimolecular reaction of 2-(4-amino-5-mercapto-4H-[1,2,4]triazol-3-yl)phenol with an aromatic or heterocyclic α-bromoacetyl derivatives is described. This synthetic procedure starts from an unprotected phenol.

Key words

triazolothiadiazines - triazolylphenol - bromomethyl ketones - polycycles - heterocycles - cyclization

Full Text

References

References and Notes

1a Molina P. Alajarin M. Pérez de Vega MJ. de la Concepción Foces-Foces M. Hernández Cano F. Claramunt RM. Elguero J. J. Chem. Soc., Perkin Trans. 1 1987; 1853
1b Holla BS. Udupa KV. Farmaco 1992; 47: 305
1c Demirbas N. Demirbas A. Karaoglu SA. Çelik E. ARKIVOC 2005; (i): 75

2a Mir I. Siddiqui MT. Comrie A. Tetrahedron 1970; 26: 5235
2b Hester JB. Ludens JH. Emmert DE. West BE. J. Med. Chem. 1989; 32: 1157
2c Holla BS. Veerendra B. Shivananda MK. Poojary B. Eur. J. Med. Chem. 2003; 38: 759

3a Spino C. Dodier M. Sotheeswaran S. Bioorg. Med. Chem. Lett. 1998; 8: 3475
3b Witaicenis A. Seito LN. Di Stasi LC. Chem.-Biol. Interact. 2010; 186: 211
3c Yang D. Gu T. Wang T. Tang Q. Ma C. Biosci., Biotechnol., Biochem. 2010; 74: 1430
3d Lee C.-R. Shin E.-J. Kim H.-C. Choi Y.-S. Shin T. Wie M.-B. Lab. Anim. Res. 2011; 27: 259
3e Yun E.-S. Park S.-S. Shin H.-C. Choi Y.-H. Kim W.-J. Moon S.-K. Toxicol. In Vitro 2011; 25: 1335
3f Kwon OS. Choi JS. Islam MN. Kim YS. Kim HP. Arch. Pharmacal Res. 2011; 34: 1561
3g Luo KW. Sun J. Chan JY.-W. Yang L. Wu SH. Fung K.-P. Liu F. Chemotherapy 2011; 57: 449
3h Huang G.-J. Deng J.-S. Liao J.-C. Hou W.-C. Wang S.-Y. Sung P.-J. Kuo Y.-H. J. Agric. Food Chem. 2012; 60: 1673

4a Talhi O. Schnekenburger M. Panning J. Pinto DG. C. A. Fernandes JA. Almeida Paz F. Jacob C. Diederich M. Silva AM. S. Bioorg. Med. Chem. 2014; 22: 3008
4b Talhi O. Abdeldjebar H. Belmiloud Y. Hassaine R. Taibi N. Válega M. Paz FA. A. Brahimi M. Bachari K. Silva AM. S. New J. Chem. 2017; 41: 10790
4c Bouhenna MM. Orlikova B. Talhi O. Schram B. Pinto DC. G. A. Taibi N. Bachari K. Diederich M. Silva AM. S. Mameri N. Anticancer Res. 2017; 37: 5225
4d Lee J.-Y. Talhi O. Jang D. Cerella C. Gaigneaux A. Kim K.-W. Lee JW. Dicato M. Bachari K. Han BW. Silva AM. S. Orlikova B. Diederich M. Cancer Lett. 2018; 416: 94

5a El-Dawy MA. Amohsen ME. O. Ismail AM. Hazaa AA. B. J. Pharm. Sci. 1983; 72: 45
5b Rao VR. Kumar VR. Vardhan VA. Phosphorus, Sulfur Silicon Relat. Elem. 1999; 152: 257

6a Lakshman AB. Gupta RL. Asian J. Chem. 2009; 21: 86
6b Lechani N. Hamdi M. Aklil F. Khabouche S. Benali Baitich O. Kheffache D. Moussi S. Ouamerali O. Eur. J. Chem. 2013; 4: 285

7a Patil RD. Joshi G. Adimurthy S. Ranu BC. Tetrahedron Lett. 2009; 50: 2529
7b Hikem-Oukacha D. Hamdi M. Silva AM. S. Rachedi Y. J. Heterocycl. Chem. 2011; 48: 63
7c Ngoy BP. Šebej P. Šolomek T. Lim BH. Pastierik T. Park BS. Givens RS. Heger D. Klán P. Photochem. Photobiol. Sci. 2012; 11: 1465
7d Benali Baitich O. Lechani N. Hamdi M. Aklil F. Khabouche S. Kheffache D. Moussi S. Ouamerali O. Eur. J. Chem. 2013; 4: 285
7e Ben Mohamed S. Rachedi Y. Hamdi M. Le Bideau F. Dejean C. Dumas F. Eur. J. Org. Chem. 2016; 2016: 2628

8 [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines 3a–e; General Procedure Equimolar amounts of the appropriate α-bromoacetyl derivative 2a–e (1.0 mmol) and triazolylphenol 1 (0.2 g; 1.0 mmol) were dissolved in absolute EtOH (10 mL) containing a catalytic amount of AcOH (1 mL), and the mixture was heated for 2 h, then cooled to r.t. The resulting solid was collected by filtration and washed with EtOH and Et₂O to give the pure product.
9 7-Hydroxy-3-[3-(2-hydroxyphenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-2H-chromen-2-one (3b) C₁₉H₁₂N₄O₄S. Green solid; yield: 0.23 g (60%); mp 239–241 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 5.00 (s, 2 H, H-7′), 6.80 (d, J = 2.2 Hz, 1 H, H-8), 6.89 (dd, J = 8.6, 2.2 Hz, 1 H, H-6), 6.93–7.01 (m, 1 H, H-5′′), 7.06 (dd, J = 8.3, 0.7 Hz, 1 H, H-3′′), 7.41–7.46 (m, 1 H, H-4′′), 7.71 (dd, J = 7.8, 1.7 Hz, 1 H, H-6′′), 7.85 (d, J = 8.6 Hz, 1 H, H-5), 8.77 (s, 1 H, H-4), 10.23 (s, 1 H, 2′′-OH), 11.33 (s, 1 H, 7-OH). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 44.0 (C-7′), 102.4 (C-8), 110.0 (C-1′′), 111.4 (C-4a), 115.1 (C-6), 117.7 (C-3′′), 117.9 (C-3), 120.1 (C-5′′), 129.3 (C-6′′), 133.6 and 133.7 (C-4′′ and C-5), 149.9 (C-4), 156.5 (C-2′′), 158.0 (C-8a), 159.6 (C-2), 163.3 (C-8′a), 164.9 (C-3′, C=N), 165.4 (C-7), 189.9 (C-6′, C=N). HRMS-ESI⁺: m/z [M + H]⁺ calcd for C₁₉H₁₃N₄O₄S: 393.0658; found: 393.0677.

Supplementary Material

Supporting Information