Rapid Boulton–Katritzky rearrangement of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles upon exposure to water and HCl
Сhemical stability of 3-(2-aminoethyl)-5-substituted 1,2,4-oxadiazoles was studied with respect to Boulton–Katritzky rearrangement, which is known to produce planar pyrazolines and pyrazoles upon heating in DMF at 150°C or without solvent at 240°C. The reactivity of 5-aryl-3-[2-(piperidin-1-yl)ethyl...
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| Published in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 54; no. 6; pp. 643 - 649 |
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| Abstract | Сhemical stability of 3-(2-aminoethyl)-5-substituted 1,2,4-oxadiazoles was studied with respect to Boulton–Katritzky rearrangement, which is known to produce planar pyrazolines and pyrazoles upon heating in DMF at 150°C or without solvent at 240°C. The reactivity of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles in one type of Boulton–Katritzky rearrangement was observed at room temperature in H
2
O, DMF + H
2
O, and in the presence of HCl. Hydrolysis of 3,5-disubstituted 1,2,4-oxadiazoles under the first two conditions gave 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium benzoates, while the action of HCl on 3,5-disubstituted 1,2,4-oxadiazoles produced their hydrochlorides along with 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium chloride hydrate. Thus, the reaction afforded spiropyrazoline compounds instead of products with a planar structure. |
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| AbstractList | Сhemical stability of 3-(2-aminoethyl)-5-substituted 1,2,4-oxadiazoles was studied with respect to Boulton–Katritzky rearrangement, which is known to produce planar pyrazolines and pyrazoles upon heating in DMF at 150°C or without solvent at 240°C. The reactivity of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles in one type of Boulton–Katritzky rearrangement was observed at room temperature in H
2
O, DMF + H
2
O, and in the presence of HCl. Hydrolysis of 3,5-disubstituted 1,2,4-oxadiazoles under the first two conditions gave 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium benzoates, while the action of HCl on 3,5-disubstituted 1,2,4-oxadiazoles produced their hydrochlorides along with 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium chloride hydrate. Thus, the reaction afforded spiropyrazoline compounds instead of products with a planar structure. Сhemical stability of 3-(2-aminoethyl)-5-substituted 1,2,4-oxadiazoles was studied with respect to Boulton-Katritzky rearrangement, which is known to produce planar pyrazolines and pyrazoles upon heating in DMF at 150°C or without solvent at 240°C. The reactivity of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles in one type of Boulton-Katritzky rearrangement was observed at room temperature in H.sub.2O, DMF + H.sub.2O, and in the presence of HCl. Hydrolysis of 3,5-disubstituted 1,2,4-oxadiazoles under the first two conditions gave 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium benzoates, while the action of HCl on 3,5-disubstituted 1,2,4-oxadiazoles produced their hydrochlorides along with 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium chloride hydrate. Thus, the reaction afforded spiropyrazoline compounds instead of products with a planar structure. Сhemical stability of 3-(2-aminoethyl)-5-substituted 1,2,4-oxadiazoles was studied with respect to Boulton–Katritzky rearrangement, which is known to produce planar pyrazolines and pyrazoles upon heating in DMF at 150°C or without solvent at 240°C. The reactivity of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles in one type of Boulton–Katritzky rearrangement was observed at room temperature in H2O, DMF + H2O, and in the presence of HCl. Hydrolysis of 3,5-disubstituted 1,2,4-oxadiazoles under the first two conditions gave 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium benzoates, while the action of HCl on 3,5-disubstituted 1,2,4-oxadiazoles produced their hydrochlorides along with 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium chloride hydrate. Thus, the reaction afforded spiropyrazoline compounds instead of products with a planar structure. |
| Audience | Academic |
| Author | Shaymardan, Esbol Kayukova, Lyudmila A. Kabdrakhmanova, Sana K. Uzakova, Asem B. Vologzhanina, Anna V. Akatan, Kydyrmolla |
| Author_xml | – sequence: 1 givenname: Lyudmila A. surname: Kayukova fullname: Kayukova, Lyudmila A. email: lkayukova@mail.ru organization: A. B. Bekturov Institute of Chemical Sciences – sequence: 2 givenname: Asem B. surname: Uzakova fullname: Uzakova, Asem B. organization: A. B. Bekturov Institute of Chemical Sciences – sequence: 3 givenname: Anna V. surname: Vologzhanina fullname: Vologzhanina, Anna V. organization: A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences – sequence: 4 givenname: Kydyrmolla surname: Akatan fullname: Akatan, Kydyrmolla organization: S. Amanzholov East Kazakhstan State University – sequence: 5 givenname: Esbol surname: Shaymardan fullname: Shaymardan, Esbol organization: S. Amanzholov East Kazakhstan State University – sequence: 6 givenname: Sana K. surname: Kabdrakhmanova fullname: Kabdrakhmanova, Sana K. organization: S. Amanzholov East Kazakhstan State University |
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| Cites_doi | 10.1055/s-0031-1289893 10.1155/2004/258712 10.1021/ol1013087 10.1007/s11094-011-0657-0 10.1039/P19820000759 10.1007/s10593-010-0597-8 10.1021/jo200066n 10.1039/c2pp25073j 10.1007/978-3-319-03979-4_34 10.1016/j.tetasy.2007.06.022 |
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| Keywords | spiropyrazolines tendency to regroup Boulton–Katritzky rearrangement hydrolysis 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles |
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| PublicationTitle | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
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| References | Kayukova, L. A.; Praliev, K. Dzh.; Agzamova, R. A.; Bismilda, V. L.; Kozhamkulov, U. A. KZ Patent 18598; Inventor Bull. Rep. Kazakhstan2010, No. 12. https://gosreestr.kazpatent.kz/. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112. Kаyukova, L. A.; Zhumadildaeva, I. S.; Praliyev, K. D. Russ. Chem. Bull., Int. Ed.2002, 51, 2100. [Izv. Akad. Nauk, Ser. Khim.2002, 1945.] YapGPAAlkortaIElgueroJJagerovicNSpectroscopy Int. J.20041860510.1155/2004/2587121:CAS:528:DC%2BD2cXpsVKks7w%3D Kayukova, L. A.; Akhelova, A. L.; Agzamova, R. A.; Bismilda, V. L.; Kozhamkulov, U. A.; Cynamon, M.; Shoen, C. In Poster Abstracts of 2006 NIAID Research Conference, Opatija, Croatia, June 24–30, 2006; Opatija, 2006, Abstr. No. 25, p. 25. Kаyukova, L. A.; Beketov, K. М.; Аkhelova, А. L.; Praliev, K. D. Chem. Heterocycl. Compd. 2006, 42, 914. [Khim. Geterotsikl. Soedin.2006, 1057.] Li, J. J. Name Reactions; Springer International Publishing: Cham, 2014, 5th ed., p. 70. Kayukova, L. A.; Orazbaeva, M. A.; Gapparova, G. I.; Beketov, K. M.; Espenbetov, A. A.; Faskhutdinov, M. F.; Tashkhodjaev, B. T. Chem. Heterocycl. Compd. 2010, 46, 879. [Khim. Geterotsikl. Soedin.2010, 1086.] Ott, G. R.; Anzalone, A. V. Synlett2011, 3018. Fyfe, M. C. T.; Gardner, L. S.; King-Underwood, J.; Procter, M. J.; Rasamison, C. M.; Schofield, K. L.; Thomas, G. H. U. S. Patent 8207147. PiccionelloAPBuscemiSVivonaNPaceAOrg. Lett.201012349110.1021/ol10130871:CAS:528:DC%2BC3cXosFaks7o%3D20614866 Piccionello, A. P.; Pace, A.; Buscemi, S.; Vivona, N. Org. Lett.2009, 11, 4018. D'AuriaMFrennaVMarulloSRacioppiRSpinelliDViggianiLPhotochem. Photobiol. Sci.201211138310.1039/c2pp25073j1:CAS:528:DC%2BC38XhtVemu7vP22722652 Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr.2009, (42), 339. Kаyukova, L. A.; Praliev, K. D.; Bismilda, V. L.; Chingisova, L. T. In 48th International Conference on Medicinal Chemistry (RICT 2012), Poitiers, France, July 4–6, 2012; Poitiers, 2012, Abstr. No. NA17, p. 117. D'AnnaFFrennaVGhelfiFMarulloSSpinelliDJ. Org. Chem.201176267210.1021/jo200066n1:CAS:528:DC%2BC3MXjtFekt7s%3D21405092 UsachevSVNikiforovGALyssenkoKANelubinaYVLevkinPAKostyanovskyRGTetrahedron: Asymmetry200718154010.1016/j.tetasy.2007.06.0221:CAS:528:DC%2BD2sXos1eisLw%3D Korbonits, D.; Kanzel-Szvoboda, I.; Horváth, K. J. Chem. Soc., Perkin Trans. 11982, 759. Kayukova, L. A.; Orazbaeva, M. A.; Petrov, A. A. In Russian Conference on Organic Chemistry, Moscow, Russia, October 25–30, 2009; Moscow, 2009, p. 215. (a) Sigma-Aldrich Handbook of Fine Chemicals 2012–2014, p. 652. (b) The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals; Budavari, S., Ed.; Merck and Co.: Rathway, 1989, p. 328. (c) NIST Chemistry WebBook, https://webbook.nist.gov/cgi/cbook.cgi?ID=C937144&Mask=80. (d) ChemicalBook Inc., https://www.chemicalbook.com/SpectrumEN_937-14-4_1HNMR.htm. Kayukova, L. A.; Beketov, K. M.; Baitursynova, G. P. In: International Сonference “Catalysis in Organic Synthesis”, September 15–20, 2012, Moscow, Russia, 2012, Abstr. No. 122, p. 214. Kayukova, L. A.; Praliev, K. D.; Akhelova, A. L.; Kemel'bekov, U. S.; Pichkhadze, G. M.; Mukhamedzhanova, G. S.; Kadyrova, D. M.; Nasyrova, S. R. Pharm. Chem. J.2011, 45(8), 468. [Khim.-Farm. Zh.2011, 45(8), 29.] (a) Spinelli, D.; Corrao, A.; Frenna, V.; Vivona, N.; Ruccia, M.; Cusmano, G. J. Heterocycl. Chem.1976, 13, 357. (b) Bottoni, A.; Frenna, V.; Lanza, C. Z.; Macaluso, G.; Spinelli, D. J. Phys. Chem. A2004, 108, 1731. Kаyukova, L. A. Chem. Heterocycl. Compd. 2003, 39, 223. [Khim. Geterotsikl. Soedin.2003, 253.] 2321_CR7 2321_CR6 2321_CR8 2321_CR21 2321_CR12 2321_CR23 SV Usachev (2321_CR19) 2007; 18 2321_CR22 2321_CR1 2321_CR3 2321_CR2 2321_CR5 2321_CR4 F D'Anna (2321_CR10) 2011; 76 AP Piccionello (2321_CR11) 2010; 12 2321_CR14 GPA Yap (2321_CR20) 2004; 18 2321_CR13 2321_CR24 2321_CR16 2321_CR15 2321_CR18 M D'Auria (2321_CR9) 2012; 11 2321_CR17 |
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| Snippet | Сhemical stability of 3-(2-aminoethyl)-5-substituted 1,2,4-oxadiazoles was studied with respect to Boulton–Katritzky rearrangement, which is known to produce... Сhemical stability of 3-(2-aminoethyl)-5-substituted 1,2,4-oxadiazoles was studied with respect to Boulton-Katritzky rearrangement, which is known to produce... |
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| SubjectTerms | Aromatic compounds Benzoates Chemistry Chemistry and Materials Science Hydrochlorides Organic Chemistry Oxadiazoles Pharmacy |
| Title | Rapid Boulton–Katritzky rearrangement of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles upon exposure to water and HCl |
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