2013
DOI: 10.1002/jhet.1034
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One‐Pot Synthesis and Characterization of Some New Types of 5,5′‐Disubstituted Bis(imidazolidine‐2,4‐diones)

Abstract: The synthesis and structural elucidation of some novel 5,5′‐disubstituted spiro and nonspiro‐bis‐hydantoins are reported. The Bucherer Burge's method has been modified for the preparation of some 5,5′‐substituted bis(imidazolidine‐2,4‐dione) derivatives starting with diketones (1–5) and dialdehydes (6, 7). In some cases, diastereoisomeric mixtures of compounds were obtained. The resulting bis‐hydantoins (8–11, 13, 14) have not to our knowledge been previously reported in the literature.

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Cited by 14 publications
(6 citation statements)
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“…In the other attempt in contribution to our previous bis-synthesis [38][39][40][41], 0.5 equivalents of prepared diketone 7, upon reaction with one equivalent of 5 and one equivalent of H 2 N-NH 2 ÁH 2 O via in situ prepared intermediate 8, in one pot led to the formation of 2,2 0 -(((butane-1,4-diylbis(oxy))bis(3,1-phenylene))bis(ethan-1-yl-1-ylidene))bis(N-phenylhydrazine-1-carboxamide) 9 (Scheme 3).…”
Section: Resultsmentioning
confidence: 98%
“…In the other attempt in contribution to our previous bis-synthesis [38][39][40][41], 0.5 equivalents of prepared diketone 7, upon reaction with one equivalent of 5 and one equivalent of H 2 N-NH 2 ÁH 2 O via in situ prepared intermediate 8, in one pot led to the formation of 2,2 0 -(((butane-1,4-diylbis(oxy))bis(3,1-phenylene))bis(ethan-1-yl-1-ylidene))bis(N-phenylhydrazine-1-carboxamide) 9 (Scheme 3).…”
Section: Resultsmentioning
confidence: 98%
“…The precipitated product was ltered, washed with H 2 O, dried, and recrystallized from EtOH to give a solid. The reaction was shown in Scheme 1 [41].…”
Section: Materials and Instrumentmentioning
confidence: 99%
“…The synthesis of the 2 [41] was obtained according to method B (Scheme 1) as a cream-powder with a high yield. The structure of 2 was con rmed by FT-IR, 1 HNMR, 13 CNMR, and Elemental analysis (C, H, O, and N).…”
mentioning
confidence: 99%
“…Here in contribution to our previous synthetic efforts , we describe one‐pot three components synthesis of 5‐substituted‐2,8‐dithioxo‐2,3,5,7,8,9‐hexahydro‐4 H ‐pyrano[2,3‐d:6,5‐d′]dipyrimidine‐4,6(1 H )‐dione derivatives via reaction of various aldehydes and thiobarbituric acid derivatives in the presence of p ‐toluenesulfonic acid ( p ‐TSA) as catalyst in EtOH under reflux condition. Recently, the application of microwaves and ultrasound in synthesis is very popular because they frequently proceed greatly faster and carry products in higher yield and ultrapurity.…”
Section: Introductionmentioning
confidence: 99%