{"data":{"id":"10.6084/m9.figshare.c.1958150.v1","type":"dois","attributes":{"doi":"10.6084/m9.figshare.c.1958150.v1","prefix":"10.6084","suffix":"m9.figshare.c.1958150.v1","identifiers":[],"alternateIdentifiers":[],"creators":[{"name":"Shen, Li-Qun","givenName":"Li-Qun","familyName":"Shen","affiliation":[],"nameIdentifiers":[]},{"name":"Tang, Yong","givenName":"Yong","familyName":"Tang","affiliation":[],"nameIdentifiers":[]},{"name":"Wu, Ai-Qun","givenName":"Ai-Qun","familyName":"Wu","affiliation":[],"nameIdentifiers":[]},{"name":"Pan, Dan","givenName":"Dan","familyName":"Pan","affiliation":[],"nameIdentifiers":[]},{"name":"Diao, Kai-Sheng","givenName":"Kai-Sheng","familyName":"Diao","affiliation":[],"nameIdentifiers":[]}],"titles":[{"title":"Synthesis, X-Ray Crystal Structure, and Computational Study of Novel Pyrazolo[3,4-B]pyridin-3-Ol Derivatives"}],"publisher":"Taylor \u0026 Francis","container":{},"publicationYear":2015,"subjects":[{"subject":"Cancer"},{"subject":"Biological Sciences"},{"subject":"Sociology"},{"subject":"FOS: Sociology","schemeUri":"http://www.oecd.org/science/inno/38235147.pdf","subjectScheme":"Fields of Science and Technology (FOS)"},{"subject":"Chemistry"},{"subject":"Biochemistry"}],"contributors":[],"dates":[{"date":"2015-12-05","dateType":"Created"},{"date":"2019-08-19","dateType":"Updated"},{"date":"2015","dateType":"Issued"}],"language":null,"types":{"ris":"GEN","bibtex":"misc","citeproc":"article","schemaOrg":"Collection","resourceType":"Collection","resourceTypeGeneral":"Collection"},"relatedIdentifiers":[{"relationType":"IsIdenticalTo","relatedIdentifier":"10.6084/m9.figshare.c.1958150","relatedIdentifierType":"DOI"}],"relatedItems":[],"sizes":[],"formats":[],"version":null,"rightsList":[{"rights":"Creative Commons Attribution 4.0 International","rightsUri":"https://creativecommons.org/licenses/by/4.0/legalcode","schemeUri":"https://spdx.org/licenses/","rightsIdentifier":"cc-by-4.0","rightsIdentifierScheme":"SPDX"}],"descriptions":[{"description":"6-(Pyrazol-1-yl)pyrazolo[3,4-b]pyridin-3-ol (\u003cb\u003e3a\u003c/b\u003e) was synthesized by cyclization reaction from 2,6-dichloro-4-methylnicotinonitrile. The related sulfonyl and acylated product (\u003cb\u003e4–7\u003c/b\u003e) were obtained from the compound \u003cb\u003e3a\u003c/b\u003e and different sulfonyl and acyl chloride compounds. The sulfonylation of the compound \u003cb\u003e3a\u003c/b\u003e afforded the O1-sulfonylation, only, to give 3-substituted products \u003cb\u003e4–6\u003c/b\u003e. The acylation of the compound \u003cb\u003e3a\u003c/b\u003e gives 1,3-diacylated products \u003cb\u003e7\u003c/b\u003e via N2, O1-diacylation. All compounds were characterized by spectroscopic methods and the molecular structures of \u003cb\u003e3a\u003c/b\u003e and \u003cb\u003e4–7\u003c/b\u003e were determined by X-ray diffraction analysis. The molecular structure of \u003cb\u003e5\u003c/b\u003e and \u003cb\u003e7\u003c/b\u003e were studied by density functional theory (DFT) calculations, reproduced the experimental geometry. The energies of the three molecules of the tautomeric forms of the compound \u003cb\u003e3a\u003c/b\u003e were calculated by DFT calculations. It was shown that the \u003cb\u003e3a\u003c/b\u003e predominated in the gas phase. Besides, molecular electrostatic potential (MESP) and frontier molecular orbital (FMO) analysis of the compound \u003cb\u003e3a\u003c/b\u003e were investigated by theoretical calculations. [Supplementary materials are available for this article. Go to the publisher's online edition of \u003ci\u003ePhosphorus, Sulfur, and Silicon and the Related Elements\u003c/i\u003e for the following free supplemental files: Additional text, tables, and figures.]","descriptionType":"Abstract"}],"geoLocations":[],"fundingReferences":[],"xml":"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