Synthesis of Pyrroles and Thiazolanes Promoted by N-Methylimidazole in Water

Abstract

A convenient and efficient approach to the synthesis of substituted pyrroles is reported based on three-component reaction of primary amines and alkyl propiolates in the presence of N-methylimidazole in water. A water-accelerated synthesis of thiazolane derivatives has also been established by employing the threecomponent reaction of primary amines, alkyl propiolates, and isothiocyanates in the presence of N-methylimidazole.

Efficient and Uncatalyzed Synthesis of Highly Functionalized New Symmetrical Indeno[1,2‐b]pyrroles via a One‐Pot Four‐Component Reaction

“…[36] Dihydroxyoxoindeno [1,2-b]pyrroles are commonly synthesized via the reaction between ninhydrin and different enamines. [37][38][39][40][41][42][43][44] In 2009, Liu and co-workers reported the cycloaddition of carbamoyl cyanides to zirconacyclocumulenes provided from Zr-catalyzed benzyne-1,3-butadiyne coupling reactions, which gave 1,8-dihydroindeno[2,1-b]pyrrole derivatives, whereas the reactions of aryl or alkyl acyl cyanides in a one-pot fashion offers a significant method for the cis-selective construction of tetrasubstituted [3]cumulenone derivaties. [45] In addition, dialkyl 1,3a,4,8b-tetrahydro-3a,8b-dihydroxy-1-alkyl-4oxoindeno[1,2-b]pyrrole-2,3-dicarboxylate derivatives were synthesized via a one-pot three-component reaction of ninhydrin, primary amines, and dialkyl acetylenedicarboxylate derivatives, reported in 2010 by Yavari et al [42] Besides, a Cu-catalyzed tandem reaction between 1-(2-iodoaryl)-2-yn-1-ones and isocyanide derivatives for the synthesis of 4-oxo-indeno [1,2-b] pyrrole derivatives via a formal [3 + 2] cycloaddition/coupling tandem process, was reported.…”

A one-pot synthesis of functionalized 4,5-bis(phenylimino)-1,3-thiazolidine-2-thiones from primary amines, CS2 and N,N’-diphenyloxalimidoyl dichloride

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activities [1], while others have found application as liquid crystals [6] and cosmetic sunscreens [7].Recently, new methods for the synthesis of 1,3-thiazole derivatives have been reported [8][9][10][11][12]. 1,3-Thiazolidine-2-thione derivatives contain a carbamodithioate moiety and have received considerable attention due to their numerous biological activities and their pivotal role in agriculture and as linkers in solid-phase organic synthesis [13][14][15].

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