Abstract:Reaction of epoxides 1 and 2 with 2-aminobenzimidazole led to formation of imidazobenzimidazol-2-ones 4 and pyrimido[1,2-a]benzimidazol-2,3-diones 5, respectively in good yields. This same compound 5 may be obtained by another route by reacting halohydrin derivates 3 with 2-aminobenzimidazole. The mechanisms of the studied reactions are discussed.
“…Along with the preparation of anagrelide scaffold containing compounds, some of its structural analogues have been reported in the literature. For instance, synthesis of 5-noranagrelide derivatives (Figure ) has been described several times by the use of traditional solution-phase synthesis and 2-aminobenzimidazole as a key intermediate (Figure ). − …”
Solid-phase synthesis of 1H-benzo[d]imidazo[1,2-a]imidazol-2(3H)-one derivatives employing Fmoc-α-amino acids and nitroaryl fluorides as key building blocks has been developed. The Fmoc-α-amino acids immobilized on Wang resin, equipped with a piperazine carbamate linker, were transformed to o-nitroanilines in two steps. After reduction of the nitro group, the corresponding o-phenylenediamines gave the 2-aminobenzimidazole scaffold by reaction either with cyanogen bromide or with Fmoc-NCS. Cleavage from the polymer support and further cyclization afforded the target compounds. The developed methodology represents a versatile and simple approach for the preparation of various corresponding 1H-benzo[d]imidazo[1,2-a]imidazol-2(3H)-ones from a large number of commercially available building blocks.
“…Along with the preparation of anagrelide scaffold containing compounds, some of its structural analogues have been reported in the literature. For instance, synthesis of 5-noranagrelide derivatives (Figure ) has been described several times by the use of traditional solution-phase synthesis and 2-aminobenzimidazole as a key intermediate (Figure ). − …”
Solid-phase synthesis of 1H-benzo[d]imidazo[1,2-a]imidazol-2(3H)-one derivatives employing Fmoc-α-amino acids and nitroaryl fluorides as key building blocks has been developed. The Fmoc-α-amino acids immobilized on Wang resin, equipped with a piperazine carbamate linker, were transformed to o-nitroanilines in two steps. After reduction of the nitro group, the corresponding o-phenylenediamines gave the 2-aminobenzimidazole scaffold by reaction either with cyanogen bromide or with Fmoc-NCS. Cleavage from the polymer support and further cyclization afforded the target compounds. The developed methodology represents a versatile and simple approach for the preparation of various corresponding 1H-benzo[d]imidazo[1,2-a]imidazol-2(3H)-ones from a large number of commercially available building blocks.
“…The encouraging biological activities of these heterocycles and in continuation of our previous work in heterocyclic chemistry on the synthesis of heterocyclic compounds containing nitrogen, sulfur, and bicyclic systems, this paper presents the synthesis of two new heterocyclic condensed compounds such as 3,5‐dioxo‐thiazolo[2,3‐a]pyrimidine‐6‐carbonitriles and 4,6‐dioxo‐pyrimido[2,1‐b][1,3]thiazine‐7‐carbonitriles from epoxides 1 and 2 . Moreover, our new route seems of interest to us and compares favorably with existing methods.…”
An easy, fast, and cheap way for the synthesis of the new 3,5‐dioxo‐thiazolo[2,3‐a] pyrimidine‐6‐carbonitriles and 4,6‐dioxo‐pyrimido[2,1‐b][1,3]thiazine‐7‐carbonitriles using epoxides α‐functionalized.
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