N-Acylcarbamates as intermediates in synthetic approaches to a bicyclic trimethylene-bridged 2,4-oxazolidinedione and hydantoin

Brouillette, Wayne J.; Smissman, Edward E.; Grunewald, Gary L.

doi:10.1021/jo01319a039

Cited by 6 publications

(4 citation statements)

References 10 publications

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“…Moreover, Smissman found that structures of bridged imides reported in the literature by other groups were incorrect (Scheme 88). 388,389 Inspired by Smissman's work, 390 in 1984, Brouillette accomplished the synthesis of bridged 2,4-oxazolinediones containing [4.2.1] and [5.2.1] ring systems using acylation of α-hydroxy lactams with aryl chloroformate as a key step (Scheme 89). 391 Thus, the reaction of lactams 330 with 4nitrophenyl chloroformate in refluxing toluene provided bridged oxazolinediones 331b−c in 44−90% yields.…”

Section: Heteroatom-containing Derivatives Of Bridged Lactamsmentioning

confidence: 99%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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CONTENTS 1. Introduction 5702 2. General Properties of Bridged Lactams 5703 2.1. Distortion Parameters of Bridged Lactams 5703 2.2. Bond Lengths of Bridged Lactams 5703 2.3. Spectroscopic Properties of Bridged Lactams 5703 2.4. Analogy of Bridged Lactams to Bridgehead Olefins 5704 2.5. Chemical and Biological Significance of Distorted Amides 5704 3. Synthesis of Historically Important Bridged Lactams 5704 3.1. Quinuclidone Derivatives 5704 3.2. Adamantanone Derivatives 5707 4. Synthesis of Bridged Lactams with the N−(CO) Bond on a Two-Carbon or Larger Bridge, ([m. (≥2).n] Type) 5708 4.1. Condensation Reactions Forming the N− C(O) Bond 5708 4.2. Heck Reactions 5711 4.3. Diels−Alder Reactions 5712 4.4. Carbene Insertion Reactions 5713 4.5. Reactions via Radical Intermediates 5714 4.6. Miscellaneous Examples 5714 5. Synthesis of Bridged Lactams with the N−(CO) Bond on a One-Carbon Bridge, ([m.1.n] Type) 5715 5.1. Carbene Insertion Reactions 5715 5.2. Schmidt Reactions 5716 5.3.

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Section: Heteroatom-containing Derivatives Of Bridged Lactamsmentioning

confidence: 99%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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“…1, 93350-08-4; 2, 93350-09-5; 3, 92288-54-5; 4, 68475-20-7; 5, 65379-06-8; 6, 87532-76-1; 7, 87532-77-2; 8, 87532-78-3; 9, 51129-01-2; 10, 93350-14-2; 11, 93350-13-1. Synthesis of (Aryloxy)alkylamines. 2. Novel Imidazo-fused Heterocycles with Calcium Channel Blocking and Local Anesthetic Activity1 Pauline J. Sanfilippo,* Maud Urbanski, Jeffery B.…”

Section: Ns23866)mentioning

confidence: 99%

Anticonvulsant activities of phenyl-substituted bicyclic 2,4-oxazolidinediones and monocyclic models. Comparison with binding to the neuronal voltage-dependent sodium channel

Brouillette¹,

Brown²,

DeLorey³

et al. 1988

J. Med. Chem.

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8,9-Dioxo-6-phenyl-1-aza-7-oxabicyclo[4.2.1]nonane (1) and 9,10-dioxo-7-phenyl-1-aza-8-oxabicyclo[5.2.1]decane (2), examples of anti-Bredt bicyclic 2,4-oxazolidinediones, were investigated as anticonvulsants in mice. Compound 2 was the more potent (anti-MES ED50 = 66 mg/kg), and its in vivo anti-MES effect was consistent with its in vitro potency of binding to the voltage-sensitive sodium channel (IC50 = 160 microM for the inhibition of binding of [3H]BTX-B), suggesting that 2 may be a new class I anticonvulsant. Several partial structures of 2, either monocyclic lactams or monocyclic 2,4-oxazolidinediones, were also evaluated in these assays, but no correlation was observed between sodium channel binding and anti-MES effects. A significant finding was that monocyclic 5-alkyl-5-phenyl-2,4-oxazolidinediones provided relatively potent, nontoxic, broad-spectrum anticonvulsants.

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“…12 The and 13C NMR assignments for 2 are presented in Table I and are consistent with the assigned structure. The reaction of 2 with Br2 and CH3OH according to the procedure of Smissman6 produced a crystalline product that was identical in every respect (mp, IR, and NMR in CF3C02H-d1) to that reported as 3. Furthermore, the electron-impact mass spectrum gave the anticipated molecular ion at m/e 356 and confirmed the presence of one bromine.…”

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confidence: 90%