Parallel Liquid-Phase Synthesis of Benzopyrano[2,3-d]pyrimidine Libraries

Abstract

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Convenient synthesis of substituted 2‐(2‐iminocoumarin‐3‐yl)thieno[2,3‐d]pyrimidin‐4‐ones

“…Following the mechanism of “recyclization” reaction, we tested whether the 2‐iminocoumarin‐3‐carbothioamides were suitable precursors for 2‐thiocoumarins synthesis. We obtained the intermediate 2‐(3‐carbamoyl‐2‐thienylimino)‐coumarin‐3‐carbothioamides 9 by reaction of 2‐iminocoumarin‐3‐carbothioamides 8 [40] with 2‐aminothiophen‐3‐carboxamides 2 in glacial acetic acid. Further “recyclization” have been performed by heating compounds 9 in DMF.…”

“…1a–d were obtained starting of malononitrile by interaction with corresponding salicylic aldehydes [42]. 2‐Iminocoumarin‐3‐carbothioamides 8a , 8b , 8c were synthesized by interaction of salicylic aldehydes of 2‐cyanoethanethioamide [40].…”

Novel approach for the synthesis of N-unsubstituted 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones

“…4,6 Synthesis of 5-hydroxymethyl-8-methyl-2-oxo-2H-pyrano[2,3-c]pyridine-3-thioamide (6e). 5-(Hydroxymethyl)-2-imino-8-methyl-2H-pyrano[2,3-c]pyridine-3-carbothioamide 7,8 (2.49 g, 0.01 mol) was suspended in a mixture of concentrated hydrochloric acid (10 ml) and ethanol (50 ml).…”

Efficient One‐Pot Synthesis of Quinazoline and Benzopyrano[2,3‐d]pyrimidine Derivatives Catalyzed by N‐Bromosulfonamides

“…Particularly, benzopyranopyrimidines are important pharmacophores that exhibit anti‐inflammatory, anti‐aggregating, anti‐platelet, analgesic, and anti‐thrombotic activities . In vivo activity by benzopyranopyrimidines have been shown in mice with P388 lymphocytic leukemia . In recent years, LiClO 4 , ionic liquid, and microwave irradiation have been utilized for synthesis of these compounds .…”