A three-component cyclocondensation reaction for the synthesis of new triazolo[1,5-a]pyrimidine scaffolds using 3-aminotriazole, aldehydes and ketene N,S-acetal.
3-Aminotriazole
Ketene acetal
Multicomponent reaction
Schiff base
Triazolo[1,5-a]pyrimidine
Journal
Molecular diversity
ISSN: 1573-501X
Titre abrégé: Mol Divers
Pays: Netherlands
ID NLM: 9516534
Informations de publication
Date de publication:
Nov 2021
Nov 2021
Historique:
received:
01
03
2020
accepted:
23
04
2020
pubmed:
11
5
2020
medline:
5
2
2022
entrez:
11
5
2020
Statut:
ppublish
Résumé
This study describes the use of 3-aminotriazole, different aldehydes and N-methyl-1-(methylthio)-2-nitroethenamine as a ketene N,S-acetal in a three-component condensation for the synthesis of a novel library of triazolo[1,5-a]pyrimidine scaffolds. The presence of trichloroacetic acid as a Brønsted-Lowry acidic promoter in acetonitrile or water solvent and room temperature condition resulting novel triazolo[1,5-a]pyrimidine systems named N-methyl-6-nitro-5-aryl-3,5-dihydro-[1, 2, 4]triazolo[1,5-a]pyrimidine-7-amine. The structure of products and direction of the N-cyclization could be confirmed using spectral data. The effect of various solvents on the progress of process was investigated in the paper. The presence of five nitrogen heteroatoms, the use of various aldehydes affording a range of skeletally distinct triazolo[1,5-a]pyrimidine-based heterocycles, the potency to create numerous hydrogen bonds in the product structure, and direction of cyclization are attractive features of this reaction.
Identifiants
pubmed: 32388702
doi: 10.1007/s11030-020-10096-0
pii: 10.1007/s11030-020-10096-0
doi:
Substances chimiques
Aldehydes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2053-2062Informations de copyright
© 2020. Springer Nature Switzerland AG.
Références
Holla BS, Mahalinga M, Karthikeyan MS, Poojary B, Akberali PM, Kumari NS (2005) Synthesis, characterization and antimicrobial activity of some substituted 1,2,3-triazoles. Eur J Med Chem 40:1173–1178
doi: 10.1016/j.ejmech.2005.02.013
Gujjar R, Marwaha A, El Mazouni F, White J, White KL, Creason S, Charman S (2009) Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice. J Med Chem 52:1864–1872
doi: 10.1021/jm801343r
Sheremet EA, Tomanov RI, Trukhin EV, Berestovitskaya VM (2004) Synthesis of 4-aryl-5-nitro-1,2,3-triazoles. Russ J Org Chem 40:594–595
doi: 10.1023/B:RUJO.0000036090.61432.18
Banu KM, Dinakar A, Ananthanarayanan C (1999) Synthesis, characterization, antimicrobial studies and pharmacological screening of some substituted 1,2,3-triazoles. Indian J Pharm Sci 61:202
Guan LP, Jin QH, Tian GR, Chai KY, Quan ZS (2007) Synthesis of some quinoline-2 (1H)-one and 1,2,4-triazolo[4,3-a]quinoline derivatives as potent anticonvulsants. J Pharm Pharm Sci 10:254–262
pubmed: 17727789
Hafez H, Abbas HA, El-Gazzar AR (2008) Synthesis and evaluation of analgesic, anti-inflammatory and ulcerogenic activities of some triazolo-and 2-pyrazolyl-pyrido[2,3-d]-pyrimidines. Acta Pharm 58:359–378
doi: 10.2478/v10007-008-0024-1
Passannanti A, Diana P, Barraja P, Mingoia F, Lauria A, Cirrincione G (1998) Pyrrolo[2, 3-d][1,2,3]triazoles as potential antineoplastic agents. Heterocycles 6:1229–1235
Manfredini S, Vicentini CB, Manfrini M, Bianchi N, Rutigliano C, Mischiati C, Gambari R (2000) Pyrazolo-triazoles as light activable dna cleaving agents. Bioorg Med Chem 8:2343–2346
doi: 10.1016/S0968-0896(00)00160-7
Johns BA, Weatherhead JG, Allen SH, Thompson JB, Garvey EP, Foster SA, Miller WH (2009) The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: establishing the pharmacophore. Bioorg Med Chem Lett 19:1802–1806
doi: 10.1016/j.bmcl.2009.01.090
Duran A, Dogan HN, Rollas S (2002) Synthesis and preliminary anticancer activity of new 1,4-dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-5H-1,2,4-triazoline-5-thiones. Farmaco 57:559–564
doi: 10.1016/S0014-827X(02)01248-X
Beasley SC, Cooper N, Gowers L, Gregory JP, Haughan AF, Hellewell PG, Naylor R (1998) Synthesis and evaluation of a novel series of phosphodiesterase IV inhibitors. A potential treatment for asthma. Bioorg Med Chem Lett 8:2629–2634
doi: 10.1016/S0960-894X(98)00490-9
De Clercq ERIK (1997) In search of a selective antiviral chemotherapy. Clin Microbiol Rev 10:674–693
doi: 10.1128/CMR.10.4.674
Weide T, Saldanha SA, Minond D, Spicer TP, Fotsing JR, Spaargaren M, Fokin VV (2010) NH-1,2,3-triazole inhibitors of the VIM-2 metallo-β-lactamase. ACS Med Chem Lett 1:150–154
doi: 10.1021/ml900022q
Chai B, Qian X, Cao S, Liu H, Song G (2003) Synthesis and insecticidal activity of 1,2,4-triazole derivatives. Arkivoc 2:141–145
doi: 10.3998/ark.5550190.0004.216
Keri RS, Patil SA, Budagumpi S, Nagaraja BM (2015) Triazole: a promising antitubercular agent. Chem Biol Drug Des 86:410–423
doi: 10.1111/cbdd.12527
Sharma V, Shrivastava B, Bhatia R, Bachwani M, Khandelwal R, Ameta J (2011) Exploring potential of 1,2,4-triazole: a brief review. Pharmacologyonline 1:1192–1222
Katritzky AR, Qi M, Feng D, Zhang G, Griffith MC, Watson K (1999) Synthesis of 1,2,4-triazole-functionalized solid support and its use in the solid-phase synthesis of trisubstituted 1,2,4-triazoles. Org Lett 1:1189–1191
doi: 10.1021/ol990186a
Murlykina MV, Morozova AD, Zviagin IM, Sakhno YI, Desenko SM, Chebanov VA (2018) Aminoazole-based diversity-oriented synthesis of heterocycles. Front Chem 6:1–43
doi: 10.3389/fchem.2018.00527
Yu J, Shi F, Gong LZ (2011) Brønsted-acid-catalyzed asymmetric multicomponent reactions for the facile synthesis of highly enantioenriched structurally diverse nitrogenous heterocycles. Acc Chem Res 44:1156–1171
doi: 10.1021/ar2000343
Hassan S, Mueller TJ (2015) Multicomponent syntheses based upon copper-catalyzed alkyne-azide cycloaddition. Adv Synth Catal 357:617–666
doi: 10.1002/adsc.201400904
Zhu QN, Zhang YC, Xu MM, Sun XX, Yang X, Shi F (2016) Enantioselective construction of tetrahydroquinolin-5-one-based spirooxindole scaffold via an organocatalytic asymmetric multicomponent [3 + 3] cyclization. J Org Chem 81:7898–7907
doi: 10.1021/acs.joc.6b01598
Guo J, Miao H, Zhao Y, Bai X, Zhu Y, Wang Q, Bu Z (2019) An unexpected multi-component one-pot cascade reaction to access furanobenzodihydropyran-fused polycyclic heterocycles. Chem Commun 55:5207–5210
doi: 10.1039/C9CC02170A
Karami B, Farahi M, Banaki Z (2015) A novel one-pot method for highly regioselective synthesis of triazoloapyrimidinedicarboxylates using silica sodium carbonate. Synlett 26:1804–1807
doi: 10.1055/s-0034-1380677
Sedash YV, Gorobets NY, Chebanov VA, Konovalova IS, Shishkin OV, Desenko SM (2012) Dotting the i’s in three-component Biginelli-like condensations using 3-amino-1,2,4-triazole as a 1,3-binucleophile. RSC Adv 2:6719–6728
doi: 10.1039/c2ra20195j
Chen Q, Jiang LL, Chen CN, Yang GF (2009) The first example of a regioselective Biginelli-like reaction based on 3-alkylthio-5-amino-1,2,4-triazole. J Heterocycl Chem 46:139–148
doi: 10.1002/jhet.1
Farghaly TA, Shawali SA, Abbas MH, Abdel-hafez AN (2015) A facile synthesis of new polyazaheterocycles via one-pot three-components condensation reaction and study of their reactions with nitrilimines. Curr Org Synth 12:95–101
doi: 10.2174/1570179411666140806005524
Shaabani A, Seyyedhamzeh M, Ganji N, Sangachin MH, Armaghan M (2015) One-pot four-component synthesis of highly substituted[1,2,4]triazolo[1,5-a]pyrimidines. Mol Divers 19:709–715
doi: 10.1007/s11030-015-9604-4
Karami B, Farahi M, Banaki Z (2015) A new protocol for catalyst-free regioselective synthesis of 5,9-dihydropyrimido[5,4-e][1,2,4]triazolo[1,5-a]pyrimidine-6,8(4H,7H)-diones. Synlett 26:741–744
doi: 10.1055/s-0034-1379953
Murlykina MV, Sakhno YI, Desenko SM, Shishkina SV, Shishkin OV, Sysoiev DO, Van der Eycken EV (2015) Study of the chemoselectivity of multicomponent heterocyclizations involving 3-amino-1,2,4-triazole and pyruvic acids as key reagents, and biological activity of the reaction products. Eur J Org Chem 2015:4481–4492
doi: 10.1002/ejoc.201500469
Komykhov SA, Bondarenko AA, Musatov VI, Diachkov MV, Gorobets NY, Desenko SM (2017) (5S,7R)-5-Aryl-7-methyl-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidin-7-ols as products of three-component condensation. Chem Heterocycl Compd 53:378–380
doi: 10.1007/s10593-017-2059-z
Gladkov ES, Sirko SM, Musatov VI, Shishkina SV, Tkachenko IG, Komykhov SA, Desenko SM (2018) New spiro derivative of dihydro-1,2,3-triazolo[1,5-a]pyrimidine as a product of multicomponent reaction. Chem Heterocycl Compd 54:1139–1144
doi: 10.1007/s10593-019-02405-9
Bayat M, Safari F, Nasri S, Hosseini FS (2019) A chemoselective synthesis and biological evaluation of novel benzo[g]thiazolo[3,2-a]quinolone derivatives. Monatsh Chem 150:703–710
doi: 10.1007/s00706-018-2337-1
Bayat M, Nasri S (2018) Synthesis and dynamic
doi: 10.1016/j.molstruc.2017.10.056
Ponra S, Majumdar KC (2016) Brønsted acid-promoted synthesis of common heterocycles and related bio-active and functional molecules. RSC Adv 6:37784–37922
doi: 10.1039/C5RA27069C
Hioe J, Šakić D, Vrček V, Zipse H (2015) The stability of nitrogen-centered radicals. Org Biomol Chem 13:157–169
doi: 10.1039/C4OB01656D