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Synthesis of 4-methoxyphenyl-substituted furo-fused derivatives

M. Benckova, A. Krutosikova, and M. Dandarova

 

Abstract: Methyl 2-(4-methoxyphenyl)-4H-furo[3,2-b]pyrrole-5-carboxylate was prepared hy thermolysis of the corresponding methyl 2-azido-3-[5-(4-methoxyphenyl)-2-furyl]propenoate. 4-Methyl and 4-benzyl derivatives were obtained using phase-transfer catalysis conditions. Methyl 2-(4-methoxyphenyl)-4H-furo[3,2-b]pyrrole-5-carboxylate with hydrazine hydrate yielded corresponding carbohydrazide, which by reaction with triethyl orthoformate or -acetate and -propionate afforded 5-substituted 2-(4-methoxyphenyl)-7H-furo[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazin-8-ones giving with phosphorus(V) sulfide thiones, reacting with hydrazine to corresponding hydrazono derivatives. The last ones with triethyl orthoformate underwent cyclization reactions leading to 9-(4-methoxyphenyl)-6-R-furo[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines.

 

Chemical Papers 51 (6B) 398–402 (1997)

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