Effective DABCO-catalyzed synthesis of new tetrazolo[1,5-a]pyrimidine analogs

Meng W, Hamann LG, Brigance RP (2006) Azolopyrimidine-based inhibitors of dipeptidyl peptidase iv and methods. Patent WO2006071752 A1 Desenko SM, Lipson VV, Gorbenko NI, Pivovarevich LP, Ryndina EN, Moroz VV, Varavin VP (1995) Synthesis and hypoglucamic activity of azolopyrimidine derivatives. ChemInform 4:265–266. doi:10.1002/chin.199544165 Dietz J, Grammenos W, Muller B, Lohmann J, Renner J, Ulmschneider S, Vrettou M (2008) Fungizide azolopyrimidine. verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel. Patent WO2008006761 A1 Grammenos W, Grote T, Huenger U, Lohmann J, Mueller B, Rack M, Rheinheimer J, Schaefer P, Schwoegler A (2006) 2-substituted 7-amino-azolopyrimidine, a method for the production and use thereof for controlling pathogenic fungi and agents containing said compound. Patent WO2006092428 A3 Schwogler A, Gewehr M, Muller B, Grote T, Grammenos W, Blasco J, Rheinheimer J, Blettner C, Schafer P, Schieweck F, Wagner O, Stierl R, Schofl U, Strathmann S, Scherer M (2007) Azolopyrimidine compounds and use thereof for combating parasitic fungi. Patent US20070197389 A1 Sirakanyan S, Geronikaki A, Spinelli D, Hovakimyan A, Noravyan A (2013) Synthesis and structure of condensed triazolo- and tetrazolopyrimidines. Tetrahedron 69:10637–10643. doi:10.1016/j.tet.2013.10.015 Hussein A, Ahmed OM (2010) Regioselective one-pot synthesis and anti-proliferative and apoptotic effects of some novel tetrazolo[1,5-a]pyrimidine derivatives. Bioorg Med Chem 18:2639–2644. doi:10.1016/j.bmc.2010.02.028 Dougherty A, Guo H, Westby G, Liu Y, Simsek E, Guo J, Mehta A, Norton P, Gu B, Cuconati A (2007) A substituted tetrahydro-tetrazolo-pyrimidine is a specific and novel inhibitor of hepatitis B virus surface antigen secretion. Antimicrob Agents Ch 51:4427–4437. doi:10.1128/AAC.00541-07 Yu W, Goddard C, Clearfield E, Mills C, Xiao T, Guo H, Morrey JD, Motter NE, Zhao K, Block TM, Cuconati A (2011) Design synthesis, and biological evaluation of triazolo-pyrimidine derivatives as novel inhibitors of hepatitis B virus surface antigen (HBsAg) secretion. J Med Chem 16:5660–5670. doi:10.1021/jm200696v Ahmed E, Ameen M, Abdel-latif F (2006) Heterocyclization of orthoaminoester and orthoa minonitrilethieno[2,3- c]pyridine: The facile synthesis of fused pyridothienopyrimidines. Phosphorus Sulfur 181:497–510. doi:10.1080/10426500500263748 Sharma RL, Kumar S, Sachar A, Singh J, Kour D (2005) Synthesis of 1,2,4-triazolo, tetrazolo and pyrazolylquinazolines. Ind J Heterocycl Chem 15:101–104 Abdelhamid AO, Al-Atoom AA (2005) 2-[4-(2-Thienyl)-1,3-thiazol-2-yl]ethanenitrile in heterocyclic synthesis of biological interist. Phosphorus Sulfur 180:1629–1646. doi:10.1080/104265090885048 Abdel-Hafez SH (2005) Selenium-containing heterocycles. synthesis and reactions of 2-amino-4,5,6,7-tetrahydro-1-benzoselenophene-3-carbonitrile with anticipated biological activity. Russ J Org Chem 41:396–401. doi:10.1007/s11178-005-0177-z Daboun H, El-Reedy AA (1983) One step synthesis of new 4-aminopyrimidine derivatives: preparation of tetrazolo- and s-triazolopyrimidines. ChemInform 13:1686–1689. doi:10.1515/znb-1983-1223 Bhuyan P, Lekhok K, Sandhu J (1999) Studies on uracils: synthesis of tetrazolo[4 0,5 0:1,6]pyrido[2,3-d ]pyrimidines by the action of cyano stabilised carbanions on 6-azido-5-formyluracils. J Chem Res. doi:10.1039/A808470J Chebanov VA, Desenko SM, Sakhno Y, Panchenko ES, Saraev VE, Musatov VI, Konev VF (2002) Heterocyclization products of arylidenepyruvic acids with 5-aminotetrazole and 2-aminobenzimidazol. Fiziol Akt Rechovini 2:10–12 Desenko SM, Gladkov ES, Komykhov SA, Shishkin O, Orlov VD (2001) Partially hydrogenated aromatic substituted tetrazolo[1,5-a]pyrimidines. Chem Heterocycl Compd 37:747–754. doi:10.1023/A:1011925631511 Metwally MA, El-Hussiny MS, El-Ablak FZ, Khalil AM (1989) Synthesis of some heterocycles of pharmaceutical interests. Pharmazie 44:261–265 Hussein A (2010) Synthesis of some new purine-related compounds: Regioselective one-pot synthesis of new tetrazolo[1,5-a]pyrimidine, pyrazolo[1,5-a]pyrimidine and pyrimido[1,6-a]pyrimidine derivatives. J Saudi Chem Soc 14:61–68. doi:10.1016/j.jscs.2009.12.010 Raju C, Madhaiyan K, Uma R, Sridhar R, Ramakrishna S (2012) Antimicrobial and antioxidant activity evaluation of tetrazolo[1,5-a]pyrimidines: a simple diisopropyl ammonium trif luoroacetate mediated synthesis. RSC Adv 31:11657–11663. doi:10.1039/C2RA21330C Yao C, Lei S, Wang C, Yu C, Tu S (2008) Solvent-free synthesis of 5-methyl-7-aryl-4, 7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic esters catalyzed by sulfamic acid. J Heterocycl Chem 6:1609–1613. doi:10.1002/jhet.5570450609 Shen S, Zhang H, Yu C, Yao C, Li T, Qin B, Lu J, Wang D (2013) Solvent-free combinatorial synthesis of tetrazolo[1,5-a]thiopyrano[3,4-d]pyrimidine derivatives. Res Chem Intermed 4:1799–1806. doi:10.1007/s11164-012-0714-7 Metwally MA, El-Hussiny MS, El-Ablak FZ, Khalil AM (1989) Synthesis of some heterocycles of pharmaceutical interest. Die Pharmazie 4:261–265 Zeng LY, Cai C (2009) Iodine catalyzed one-pot multicomponent synthesis of a library of compounds containing tetrazolo[1,5-a]pyrimidine core. J Comb Chem 12:35–40. doi:10.1021/cc9000983 Yang H, Tian R, Li Y (2008) Organic reactions catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO). Front Chem China 3:279–287. doi:10.1007/s11458-008-0049-5 Bita B (2010) 1,4-Diazabicyclo[2.2.2]octane (DABCO) as a useful catalyst in organic synthesis. Eur J Chem 1:54–60. doi:10.5155/eurjchem.1.1.54-60.2 Dalko PI, Moisan L (2001) Asymmetrische Organokatalyse. Angew Chem 20:3840–3864. doi:10.1002/1521-3757(20011015)113:20<384020 Dalko PI, Moisan L (2004) Im Goldenen Zeitalter der Organokatalyse. Angew Chem 39:5248–5286. doi:10.1002/ange.200400650 Ghorbani-Vaghei R, Rahmatpour F, Sarmast N, Mahmoudi J, Shahriari A (2017) DABCO as a green catalyst for the synthesis of pyranoquinoline derivatives. Can J Chem 999:1–4. doi:10.1139/cjc-2016-0537 Jain S, Paliwal PK, Babu GN, Bhatewara A (2014) DABCO promoted one-pot synthesis of dihydropyrano (c) chromene and pyrano[2,3-d]pyrimidine derivatives and their biological activities. J Saudi Chem Soc 5:535–540. doi:10.1016/j.jscs.2011.10.023 Singh M, Fatma S, Ankit P, Singh SB, Singh J (2014) Boric acid in aqueous micellar medium: an effective and recyclable catalytic system for the synthesis of aryl-7,8-dihydro [1,2,4]triazolo[4,3-a]pyrimidine-6-carbonitriles. Tetrahedron Lett 2:525–527. doi:10.1016/j.tetlet.2013.11.090 Kappe T, Roschger P, Farber G (1993) Synthesis and reactions of tetrazolo[1,5-\(\alpha \)] pyrimidines. J Heterocycl Chem 5:1267–1271. doi:10.1002/jhet.5570300516 Tisler M (1973) Some aspects of azido-tetrazolo isomerization. Synthesis 3:123–126. doi:10.1055/s-1973-22145