caa a22 4500 445876360 CHVBK 20180317145529.0 cr unu---uuuuu 170323e20110601xx s 000 0 eng 10.1007/s10593-011-0760-x doi (NATIONALLICENCE)springer-10.1007/s10593-011-0760-x C-C recyclizations of some 2,7-disubstituted 6-ethoxycarbonylpyrazolo[1,5- a ]pyrimidines [Elektronische Daten] [G. Danagulyan, A. Boyakhchyan, A. Danagulyan, H. Panosyan] Condensation of ethyl ethoxymethyleneacetoacetate and ethyl ethoxymethylenecyanoacetate in ethanol with 3-substituted 3-aminopyrazoles and 5-amino-1,2,4-triazole gave the 2-substituted 6-ethoxy- carbonyl-7-methyl- and 7-amino-6-ethoxycarbonylpyrazolo[1,5-a]pyrimidines as well as 7-amino-6-ethoxycarbonyl-1,2,4-triazolo[1,5-a]pyrimidine. In the presence of alkali these rearranged to 2-substituted 6-acetyl-7-hydroxy- and 6-carbamoyl-7-hydroxypyrazolo[1,5-a]pyrimidines respectively and also to 6-carbamoyl-7-hydroxy-1,2,4-triazolo[1,5-a]pyrimidine. According to 1H (including NOESY) NMR spectroscopic data there were formed, along with the cyclization products, noncyclic condensation adducts (as cyano derivatives) from ethyl ethoxymethylenecyanoacetate with 5-aminopyrazoles. In the presence of alcoholic alkaline solution these were also transformed in high yield to 6-carbamoyl-7-hydroxypyrazolopyrimidines. When refluxed for a longer time in 12% aqueous alcoholic alkaline solution the 6-ethoxycarbonyl-2,7-dimethylpyrazolo[1,5-a]pyrimidine and 6-acetyl-7-hydroxy-2-methylpyrazolo[1,5-a]pyrimidine recyclize to give 6-carboxy-2,7-dimethyl- and 2,7-di- methylpyrazolo[1,5-a]pyrimidines. Springer Science+Business Media, Inc., 2011 pyrazolo[1,5- a ]pyrimidine nationallicence 1,2,4-triazolo[1,5- a ]pyrimidine nationallicence rearrangement nationallicence recyclization nationallicence Danagulyan G. Russian-Armenian (Slavonic) State University, 123 Hovsep Emin St., 0091, Yerevan, Republic of Armenia aut Boyakhchyan A. Institute of Organic Chemistry, Scientific-Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 167-A Zakariya Kanakertsi St., 0094, Yerevan, Republic of Armenia aut Danagulyan A. Institute of Organic Chemistry, Scientific-Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 167-A Zakariya Kanakertsi St., 0094, Yerevan, Republic of Armenia aut Panosyan H. Molecular Structure Research Center, Scientific-Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatunyan Ave, 0014, Yerevan, Republic of Armenia aut Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/3(2011-06-01), 321-331 0009-3122 47:3<321 2011 47 10593 https://doi.org/10.1007/s10593-011-0760-x text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10593-011-0760-x text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Danagulyan G. Russian-Armenian (Slavonic) State University, 123 Hovsep Emin St., 0091, Yerevan, Republic of Armenia aut NATIONALLICENCE 700 1- Boyakhchyan A. Institute of Organic Chemistry, Scientific-Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 167-A Zakariya Kanakertsi St., 0094, Yerevan, Republic of Armenia aut NATIONALLICENCE 700 1- Danagulyan A. Institute of Organic Chemistry, Scientific-Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 167-A Zakariya Kanakertsi St., 0094, Yerevan, Republic of Armenia aut NATIONALLICENCE 700 1- Panosyan H. Molecular Structure Research Center, Scientific-Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatunyan Ave, 0014, Yerevan, Republic of Armenia aut NATIONALLICENCE 773 0- Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/3(2011-06-01), 321-331 0009-3122 47:3<321 2011 47 10593 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer