Utility of [4-(3-methoxyphenyl)pyrimidin-2-yl]cyanamide in synthesis of some heterocyclic compounds,Journal of Heterocyclic Chemistry

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Utility of [4-(3-methoxyphenyl)pyrimidin-2-yl]cyanamide in synthesis of some heterocyclic compounds
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2021-06-18 , DOI: 10.1002/jhet.4324
Bahgat R. M. Hussein ₁ , A. Khodairy ₁

Affiliation

N-[4-(3-Methoxyphenyl)pyrimidin-2-yl]cyanamide (1) was reacted with morpholine and respective binuclephilic reagents namely: ethylenediamine, o-phenylenediamine, o-aminothiophenol, or o-aminophenol to give the corresponding carboximidamide 2, imidazolidine 3, and benzazoles 4–6. While its reaction with hydrazides in DMF at 90°C, gave the corresponding 1,2,4-triazols 7–11. Also, treatment of cyanamide 1 with heterocycles having both nucleophilic and electrophilic groups (─NH₂/─COOEt) in iso-propanol in presence of catalytic amount of Conc. HCl, gave the corresponding thieno[2,3-d]pyrimidinone 12 and unexpected thieno[3,2-d]pyrimidine 13 instead of bis-thieno[3,2-d]pyrimidine 14, respectively. While, its reaction with ethyl 5-amino-1,3-thiazole-4-carboxylate yielded the unexpected N-(pyrimidin-2-yl)urea 15 rather than the corresponding thiazolo[5,4-d]pyrimidine 16. Unexpected N-(pyrimidin-2-yl)thiourea 17 was obtained, when cyanamide 1 reacted with potassium thiolates in iso-propanol with catalytic amount of Conc. HCl.

中文翻译：

[4-(3-甲氧基苯基)嘧啶-2-基]氰胺在一些杂环化合物合成中的应用

ñ - [4-（3-甲氧基苯基）嘧啶-2-基]氰胺（1）与吗啉和相应的试剂binuclephilic即进行反应：乙二胺，Ó苯二胺，Ò -aminothiophenol，或ö氨基苯酚，得到相应的甲脒2、咪唑烷3和苯并唑4–6。在 90°C 下，它在 DMF 中与酰肼反应，得到相应的 1,2,4-三唑7-11。此外，治疗氰胺1与具有亲核和亲电基团（─NH杂环₂中/─COOEt）异-丙醇存在催化量的浓度。HCl，分别得到相应的噻吩并[2,3- d ]嘧啶酮12和意外的噻吩并[3,2- d ]嘧啶13，而不是双-噻吩并[3,2- d ]嘧啶14。同时，它与 5-氨基-1,3-噻唑-4-羧酸乙酯的反应产生了意想不到的N- (嘧啶-2-基)脲15而不是相应的噻唑并[5,4- d ]嘧啶16。意想不到ñ -硫脲（嘧啶-2-基）17获得，当氰胺1与硫醇钾在异丙醇中与催化量的 Conc 反应。盐酸。

更新日期：2021-06-18

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