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Vol. 29 No. 12 (2017): Vol 29 Issue 12

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Microwave Assisted Gould-Jacob Reaction in the Synthesis of Furopyrimidopyrimidines and Their Transformation via Ring Opening to Aminoesters

https://doi.org/10.14233/ajchem.2017.20873
Nirmal M. Shah
Department of Chemistry, M.G. Science Institute, Navrangpura, Ahmedabad-380 009. India
Vivek C. Ramani
Department of Chemistry, M.G. Science Institute, Navrangpura, Ahmedabad-380 009. India
Rina D. Shah
Department of Chemistry, M.G. Science Institute, Navrangpura, Ahmedabad-380 009. India

Corresponding Author(s) : Rina D. Shah

drrdshah@yahoo.co.in

Asian Journal of Chemistry, Vol. 29 No. 12 (2017): Vol 29 Issue 12

Abstract

Gould-Jacob reaction is well-known for the construction of fused pyrimidopyrimidines from pyrimidineamines and diethyl ethoxymethylenemalonate (EMME) or acyl malonic ester. Ethyl 4-oxo-8,9-disubstitutedfuro[3,2-e]pyrimidine-3-carboxylates (3) has been carried out by classical heating from furo[2,3-d]pyrimidine-4-amines (1) and diethyl ethoxymethylenemalonate through the formation of uncyclized diethyl N-[5,6-substituted-7H-[2,3-d]pyrimidin-4-yl]aminomethylenemalonates (2) as an intermediate. The identical compound 3 have also been synthesized via rapid solvent free microwave irradiation method. A comparison of classical method versus solvent-free microwave irradiation method has been studied. The reaction of compound 3 has also been explored with alcoholic NaOH and hydrazine hydrate to synthesize corresponding acid 4 and acid hydrazide derivatives 5. Reaction of compound 3 with hydrazine hydrate failed to yield acid hydrazide, but they underwent unexpected ring opening and transformed to respective aminoester 6.

Keywords

Gould-Jacob reaction Furopyrimidopyrimidines Ethoxymethylene malonate Alkaline hydrolysis Aminoesters
Shah, N. M., Ramani, V. C., & Shah, R. D. (2017). Microwave Assisted Gould-Jacob Reaction in the Synthesis of Furopyrimidopyrimidines and Their Transformation via Ring Opening to Aminoesters. Asian Journal of Chemistry, 29(12), 2750–2754. https://doi.org/10.14233/ajchem.2017.20873
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