Selective cyclization modes of methyl 3 '-heteroarylamino-2 '-(2,5-dichlorothiophene-3-carbonyl)acrylates. Synthesis of model (thienyl) pyrazolo- and triazolo[1,5-alpha]pyrimidines

Sweidan Nuha I; El-Abadelah Mustafa M.; Nazer Musa Z.; Voelter Wolfgang

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Selective cyclization modes of methyl 3 '-heteroarylamino-2 '-(2,5-dichlorothiophene-3-carbonyl)acrylates. Synthesis of model (thienyl) pyrazolo- and triazolo[1,5-alpha]pyrimidines

机译：甲基3'-丙芳基-2' - （2,5-二氯噻吩-3-羰基）丙烯酸酯的选择性环化模式。模型（噻吩基）吡唑和三唑的合成[1,5-α]嘧啶

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摘要

Interaction of methyl 3-ethoxy-2-(2,5-dichloro-3-thenoyl)acrylate (I) with 3-aminopyrazole and 3- amino-1,2,4-triazole generated the respective pyrazolo [1,5-alpha]pyrimidine (4) and triazolo[1,5-alpha]pyrimidine (7). The formation of 4 entails selective and consecutive displacement of the 3-ethoxy and methoxy (ester) anions in I by 3-NH2 and 1-NH of 3-aminopyrazole. On the other hand, the formation of 7 implies selective displacement of 3-ethoxy in I by the ring-NH followed by cyclocondensation involving the keto group in I and 3-NH2 of aminotriazole. This latter selective displacement sequence is also followed by 3-amino-5-hydroxypyrazole in its reaction with I. The structures of the new compounds are supported by microanalytical and spectral data.

机译：甲基3-乙氧基-2-（2,5-二氯-3-乙烯基）丙烯酸酯（I）与3-氨基吡唑和3-氨基-1,2,4-三唑的相互作用生成相应的吡唑并[1,5-α]嘧啶（4）和三唑并[1,5-α]嘧啶（7）。4的形成需要3-氨基吡唑的3-NH2和1-NH选择性和连续置换I中的3-乙氧基和甲氧基（酯）阴离子。另一方面，7的形成意味着I中的3-乙氧基被环NH选择性置换，然后是涉及I中酮基和氨基三唑的3-NH2的环缩合。后一个选择性置换序列之后还有3-氨基-5-羟基吡唑与I的反应。新化合物的结构由显微分析和光谱数据支持。

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来源
《Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences》 |2020年第12期|共6页
作者
Sweidan Nuha I; El-Abadelah Mustafa M.; Nazer Musa Z.; Voelter Wolfgang;
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作者单位

Univ Petra Fac Art &

Sci Dept Chem Amman 961343 Jordan;

Univ Jordan Fac Sci Dept Chem Amman 11942 Jordan;

Univ Jordan Fac Sci Dept Chem Amman 11942 Jordan;

Univ Tubingen Interfak Inst Biochem Hoppe Seyler Str 4 D-72076 Tubingen Germany;

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正文语种 eng
中图分类化学;
关键词
3-aminopyrazole; 3-amino-5-hydroxypyrazole; 3-amino-1; 2; 5-triazole; 3-ethoxy-2-(3-thenoyl)acrylate; selective SN cyclization sequence;

机译：3-氨基吡唑;3-氨基-5-羟基吡唑;3-氨基-1;2;5-三唑;3-乙氧基-2-（3-单酰基）丙烯酸酯;选择性SN环化序列;

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机译：将三唑和四唑体系连接到吡咯并[2,3-d]嘧啶上：四唑并[1,5-c] - 吡咯并[3,2-e] - 嘧啶和三唑并[1,5-c]吡咯并[]的合成3,2-e]嘧啶作为潜在的抗菌剂

Selective cyclization modes of methyl 3 '-heteroarylamino-2 '-(2,5-dichlorothiophene-3-carbonyl)acrylates. Synthesis of model (thienyl) pyrazolo- and triazolo[1,5-alpha]pyrimidines

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