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On the reaction of 2-[(4-cyano-5,6,7,8-tetrahydroisoquinolin-3-yl)oxy]acetamides with bases: 1-amino-6,7,8,9-tetrahydrofuro[2,3-c]isoquinoline-2-carboxamides and 3-amino-4-cyano-5,6,7,8-tetrahydroisoquinolines via a Smiles-type rearrangement

“…Moreover the observed rearrangement gave a new method for the synthesis of 3-aminoisoquinolines 6 and pyrazolo [3,4-b]pyridines 8, compounds interesting from a biological point of view. 26 Although this rearrangement did not provide yields of amino derivatives 6 and pyrazolo[3,4-b]pyridines 8 higher than those of the method from the chloro derivatives 9 (comparable yields with the two methods were observed), this pathway of synthesis appeared more affordable and, importantly, avoids the chlorination reaction, which is often difficult. Quoted values are in the range ±0.4% of the theoretical ones.…”

Synthesis, Antitumor Activity, and Docking Analysis of New Pyrido[3′,2′:4,5]furo(thieno)[3,2-d]pyrimidin-8-amines

“…Here, 3-chloro-1-(2-furyl)-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile ( 1 ) [19] was used as a starting compound: it was treated with ethyl mercaptoacetate in the presence of sodium ethoxide, thus obtaining ethyl 1-amino-5-(2-furyl)-6,7,8,9-tetrahydrothieno[2,3- c ]isoquinoline-2-carboxylate ( 2 ). The presence of two functional groups in the thiophene ring of compound 2 allowed for the cyclocondensation of the latter through the action of formamide.…”

“…Melting points were determined on a Boetius microheating stage. Compounds 1 [19] , 6 [13] , and 7a , b , d , h , i , k [13,20] have already been described.…”

Synthesis of New Heterocyclic Systems: Pyrido[3′,2′:4,5]thieno(furo)[2,3‐e][1,2,4]triazolopyrimidines and an Unusual ANRORC Rearrangement in the Fused Pyrimidine Series

“…Literature data indicate that derivatives of carbocyclo‐ and heterocyclo[ c ]pyridines can show interesting pharmacological activity. For example, the bicyclic pyrano[3,4‐ c ]pyridines show high cardiotonic activity, the tricyclic fused pyrazolo[3,4‐ b ]pyridines display anticonvulsant activity and are EPHA4 inhibitors, while the tetracyclic derivatives of pyrido[3′,2′:4,5]thieno(furo)[3,2‐ d ]pyrimidine appear to be able to interact with a number of molecular targets including phosphodiesterase IV with potential use in the treatment of asthma and chronic obstructive pulmonary disease, release control of tumor necrosis factor‐α (TNFα), beta2 adrenoreceptor agonist activity and pronounced antimicrobial activity . Finally the pentacyclic derivatives of pyrido[3′,2′:4,5]furo[3,2‐ d ]pyrimidines exhibit pronounced neurotropic activity …”