An easy synthesis of 5-functionally substituted ethyl 4-amino-1-aryl- pyrazolo-3-carboxylates: interesting precursors to sildenafil analogues
نویسندگان
چکیده
3-Oxo-2-arylhydrazononitriles 1a-c react readily with chloroacetonitrile, ethyl chloroacetate, and with phenacyl chloride to give 4-aminopyrazoles 4a-e. The pyrazolo[4,3-d]pyrimidine derivatives 7 and 10 are synthesized via reaction of the aminopyrazole 4b with phenylisothiocyanate and DMFDMA/NH4OAc respectively.
منابع مشابه
Efficient one-pot synthesis of 6-amino-4-aryl-5-cyano-2-methyl-4H-pyran-3-carboxylates catalyzed by nano MgO in water
Water is a versatile solvent in many ways, and in this sense performing organic reactions in this medium is now of great interest. The one-pot reaction of ethyl acetoacetate or benzyl acetoacetate, with benzaldehydes and malononitrile to provide some novel 6-amino-4-aryl-5-cyano-2-methyl-4H-pyran-3-carboxylates has been performed over nano MgO with high performance in water as a green solvent a...
متن کاملMicrowave assisted synthesis of some new thiazolopyrimidine, thiazolodipyrimidine and thiazolopyrimidothiazolopyrimidine derivatives with potential antioxidant and antimicrobial activity.
Biginelli reaction of ethyl acetoacetate, thiourea and the appropriate aromatic aldehyde was used to produce ethyl 4-aryl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates, that reacted with bromomalononitrile to give ethyl 3-amino-5-aryl-2-cyano-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates rather than the isomeric 7H-thiazolo[3,2-a]pyrimidines. Thiazolopyrimidine derivative...
متن کاملSynthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using nanocrystalline ZnZr4(PO4)6 ceramics as an efficient catalyst
Nanocrystalline ZnZr4(PO4)6 ceramics as an efficient catalyst have been used for the preparation of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates by the four component reaction of dimethylacetylenedicarboxylate, hydrazinehydrate, malononitrile and aromatic aldehydes in water at room temperature. In this research Nano-ZnZr4(PO4)6 coordinate with the active groups(...
متن کاملSynthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using nanocrystalline ZnZr4(PO4)6 ceramics as an efficient catalyst
Nanocrystalline ZnZr4(PO4)6 ceramics as an efficient catalyst have been used for the preparation of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates by the four component reaction of dimethylacetylenedicarboxylate, hydrazinehydrate, malononitrile and aromatic aldehydes in water at room temperature. In this research Nano-ZnZr4(PO4)6 coordinate with the active groups(...
متن کاملSelenium-Containing Heterocycles From Isoselenocyanates: Synthesis of Ethyl 4-Oxo-2-amino-4,5-dihydroselenophene-3-carboxylates
Aryl and alkyl isoselenocyanates 2 react with ethyl �-chloroacetoacetate (1) in the presence of triethylamine to give the corresponding 4-oxo-2-amino-4,5-dihydroselenophene-3-carboxylates 4a-f in moderate to good yields. DOI: https://doi.org/10.2174/157017807780037342 Posted at the Zurich Open Repository and Archive, University of Zurich ZORA URL: https://doi.org/10.5167/uzh-50685 Accepted Vers...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Beilstein Journal of Organic Chemistry
دوره 3 شماره
صفحات -
تاریخ انتشار 2007