Hydrophobicity change on N-oxidation of some 4-aminoquinolines.

Go, Mei‐Lin; Ngiam, Tong Lan

doi:10.1248/cpb.36.1393

Cited by 2 publications

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“…However, our attempts to synthesize a corresponding hydantoin with a 5-phenylcarbamoyl rest as the only substituent failed. The proline-derived diester 5 [6,7] (Scheme 2) was prepared from 1c (Scheme 1) and 1,3-dibromopropane with benzyltriethylammonium chloride as phase transfer catalyst [7]. The utilization of 5 as the substrate of the aforementioned conversions let us anticipate interesting products.…”

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Transformation of a spirobarbituric acid via aminobarbituric acid‐hydantoin rearrangement

Ambrozak¹,

Güutschow²

2006

Journal of Heterocyclic Chem

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A successful application of the aminobarbituric acid‐hydantoin rearrangement to produce a bicyclic carbamoylhydantoin from an intermediate spirobarbituric acid is reported. 7a‐Phenylcarbamoyl‐tetrahydro‐1H‐pyrrolo[1,2‐c]imidazole‐1,3(2H)‐dione (8) was obtained in a one‐pot multistep reaction of 1‐acetyl‐2,2‐bis(ethoxycarbonyl)pyrrolidine (5) and phenylurea in the presence of sodium ethoxide. Under less severe conditions, 5 and phenylurea were reacted to afford 1‐acetyl‐7‐phenyl‐triaza[4,5]decane‐6,8,10‐trione (6). The structural elucidation of the bicyclic hydantoin 8 and the spirobarbituric acid 6 was based on relevant nmr signals in accordance with those of reference compounds, i.e. monocyclic hydantoins 4a,b and acetamidobarbituric acids 2a‐c. The latter compounds were newly prepared from diethyl acetamidomalonates 1 and phenylurea.

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confidence: 99%