Abstract
2-Aryl [1,2,4]triazolo[1,5-d][1,2,4]triazine-5(6H)-thiones were methylated using methyl iodide in the presence of NaOH to give the corresponding 5-methylthio derivatives. Upon treatment with hydrazine hydrate, the latter were transformed to the corresponding 5-hydrazino derivatives via nucleophilic displacement. The 5-hydrazino compounds were reacted with orthoesters to furnish a novel heterocyclic system, bis[1,2,4]triazolo[4,3-b:1′,5′-d][1,2,4]triazines.
Graphical abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Rusinov VL, Ulomskii EN, Chupakhin ON, Charushin VN (2008) Russ Chem Bull 57:985
Wooly DW, Shaw E (1951) J Biol Chem 189:401
Dornow A, Menzel H, Marx P (1964) Chem Ber 97:2173
Shawali AS, Gomha SM (2002) Tetrahedron 58:8559
Mironovich LM, Ivanov MA (2003) Chem Heterocycl Compd 39:1207
Hurst DT (1995) Six-membered ring systems: triazines, tetrazines, and fused ring polyaza systems. In: Suschitzy H, Scriven EFV (eds) Progress in heterocyclic chemistry, vol 7. Elsevier, Amsterdam, p 244
Groger H, Sans J, Guthner T (2000) Chim Oggi 18:12
Lhassani M, Chavignon O, Chezal JM, Teulade JC, Chapat JP, Snoeck R, Andrei G, Balzarini J, De Clercq E, Gueiffier A (1999) Eur J Med Chem 34:271
Ulomskii EN, Deev SL, Shestakova TS, Rusinov VL, Chupakhin ON (2002) Russ Chem Bull 51:1737
Raw SA, Taylor RJK (2010) Recent advances in the chemistry of 1,2,4-triazines. In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 100. Elsevier, Amsterdam, p 75
Kumar R, Sirohi TS, Singh H, Yadav R, Roy RK, Chaudhary A, Pandeya SN (2014) Mini Rev Med Chem 14:168
Trust RI, Albright JD, Lovell FM, Perkinson NA (1979) J Heterocycl Chem 16:1393
Taha MAM, El-Badry SM (2008) Monatsh Chem 139:1261
Heravi MM, Fathi Vavsari V (2015) Recent advances in application of amino acids: key building blocks in design and synthesis of heterocyclic compounds. In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 114. Elsevier, Amsterdam, p 77
Heravi MM, Talaei B (2015) Ketenes as privileged synthons in the synthesis of heterocyclic compounds, part 2: five-membered heterocycles. In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 114. Elsevier, Amsterdam, p 147
Heravi MM, Alishiri T (2014) Dimethyl acetylenedicarboxylate as a building block in heterocyclic synthesis. In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 113. Elsevier, Amsterdam, p 1
Heravi MM, Talaei B (2014) Ketenes as privileged synthons in the synthesis of heterocyclic compounds. Part 1: three- and four-membered heterocycles. In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 113. Elsevier, Amsterdam, p 143
Heravi MM, Khaghaninejad S, Mostofi M (2014) Pechmann reaction in the synthesis of coumarin derivatives. In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 112. Elsevier, Amsterdam, p 1
Heravi MM, Khaghaninejad S, Nazari N (2014) Bischler–Napieralski reaction in the synthesis of isoquinolines. In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 112. Elsevier, Amsterdam, p 183
Heravi MM, Aghapoor K, Nooshabadi MA, Mojtahedi MM (1997) Monatsh Chem 128:1143
Heravi MM, Sadjadi S, Oskooie HA, Hekmatshoar R, Bamoharram FF (2008) Catal Commun 9:470
Khaghaninejad S, Heravi MM (2014) Paal–Knorr reaction in the synthesis of heterocyclic compounds. In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 111. Elsevier, Amsterdam, p 95
Heravi MM, Mousavizadeh F, Ghobadi N, Tajbakhsh M (2014) Tetrahedron Lett 55:1226
Heravi MM, Moghimi S (2012) Tetrahedron Lett 53:392
Ghassemzadeh M, Bolourtchian M, Chitsaz S, Neumuller B, Heravi MM (2000) Eur J Inorg Chem 1877
Heravi MM, Bamoharram FF, Rajabzadeh G, Seifi N, Khatami M (2006) J Mol Catal A Chem 259:213
Heravi MM, Rajabzadeh G, Bamoharram FF, Seifi N (2006) J Mol Catal A Chem 256:238
Heravi MM, Keivanloo A, Rahimizadeh M, Bakavoli M, Ghassemzadeh M (2004) Tetrahedron Lett 45:5747
Heravi MM, Montazeri N, Rahimizadeh M, Bakavoli M, Ghassemzadeh M (2005) J Heterocycl Chem 42:1021
Acknowledgments
We acknowledge the financial support from Research Council of Islamic Azad University, Tonekabon branch and Alzahra University, Tehran, Iran.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Montazeri, N., Heravi, M.M., Tajfirooz, F. et al. Synthesis of bis[1,2,4]triazolo[4,3-b:1′,5′-d][1,2,4]triazine, a novel polynitrogenated heterocyclic system. Monatsh Chem 148, 691–694 (2017). https://doi.org/10.1007/s00706-016-1810-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-016-1810-y