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Synlett
Volumn , Issue 8, 2007, Pages 1269-1273
Alkylidenephosphoranes in heterocyclic synthesis: Reactivity of benzoxazinones with resonance-stabilized phosphorus ylides
Author keywords

Heteroring transformations; Isatoic anhydrides; Quinoline derivatives; Resonance stabilized alkylidenephosphoranes
Indexed keywords

ALKYLIDENEPHOSPHORANE DERIVATIVE; BENZAZEPINE DERIVATIVE; BENZOXAZINONE DERIVATIVE; FURAN DERIVATIVE; INDANONE DERIVATIVE; PHOSPHORANE DERIVATIVE; PHOSPHORUS; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;
EID: 34249777546     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977459     Document Type: Article
Times cited : (6)
References (29)
  • 9
    • 85069762576 scopus 로고
    • and references cited therein
    • (a) Coppola, G. M. Synthesis 1980, 505; and references cited therein.
    • (1980) Synthesis , pp. 505
    • Coppola, G.M.1
  • 20
    • 34249815609 scopus 로고    scopus 로고
    • Typical Procedure for the Reaction of Isatoic Anhydrides 1a,b with Ester Ylides 6a,b (a) In dioxane: A mixture of alkoxycarbonylmethylene (triphenyl)phosphorane 6a (or 6b, 5.2 mmol) and 1a (or 1b, 4.9 mmol) in 40 mL dry dioxane w as heated under reflux for 3 d. After removal of the solvent, EtOAc (30 mL) was added. The material that precipitated was collected and crystallized from EtOAc-CH 2Cl2 to give the known ylide 7a (from the reaction of 6a,b with 1a; ca. 38, mp >300°C (from acetone; lit.3b mp 320°C, or 7b (from the reaction of 6a,b with 1b; ca. 40, mp 252-254°C [from acetone-Et2O (2:1, lit.3b mp 252-253°C, from EtOAc-CH2Cl2, Components present in the filtrate w ere separated by column chromatography on silica gel. Compounds 1a and 6a: Elution with n-hexane- EtOAc (3:7 v/v) ga
    • 10 mp. 166-167°C, from benzene]. The second fraction (n-hexane-EtOAc, 3:7 v/v) gave straw-colored crystals of diethyl 2,5-dihydroxy-1-methylbenzazepine-3,4-dicarboxylate (15d, 303 mg, 22%), mp 142-144°C (from benzene). Percentage yields, physical and spectral data of the new products 15a-d are listed in Table 1.
  • 21
    • 34249791302 scopus 로고    scopus 로고
    • In EtOAc with benzoic acid; The same reaction between ester ylides 6a,b (7.5 mmol) and 1a,b (4.9 mmol) was repeated in EtOAc containing benzoic acid (0.3 g, heating under reflux for 2 d. After the usual workup, yellow crystals of 13a (313 mg, 28% yield) and 15a (720 mg, 46, from 6a and 1a, 13b (279 mg, 28% yield) and 15b (728 mg, 51, from 6b and 1a, 13c (334 mg, 30% yield) and 15c (662 mg, 44, from 6a and 1b, and 13d (263 mg, 25% yield) and 15d (662 mg, 48, from 6b and 1b) were obtained. All products were identified by mixed mp as well as comparison of IR and mass spectral data with those of the materials previously obtained. Compounds 7a,b were not isolated from this reaction
    • (b) In EtOAc with benzoic acid; The same reaction between ester ylides 6a,b (7.5 mmol) and 1a,b (4.9 mmol) was repeated in EtOAc containing benzoic acid (0.3 g), heating under reflux for 2 d. After the usual workup, yellow crystals of 13a (313 mg, 28% yield) and 15a (720 mg, 46%, from 6a and 1a), 13b (279 mg, 28% yield) and 15b (728 mg, 51%, from 6b and 1a), 13c (334 mg, 30% yield) and 15c (662 mg, 44%, from 6a and 1b), and 13d (263 mg, 25% yield) and 15d (662 mg, 48%, from 6b and 1b) were obtained. All products were identified by mixed mp as well as comparison of IR and mass spectral data with those of the materials previously obtained. Compounds 7a,b were not isolated from this reaction.
  • 26
    • 34249811011 scopus 로고    scopus 로고
    • Typical Procedure for the Reaction of Isatoic Anhydrides 1a,b with Keto Ylides 16a,b A solution of acetylmethylene(triphenyl)phosphorane (4.9 mmol) and 1a (or 1b, 5.2 mmol) in 40 mL EtOAc containing benzoic acid was refluxed for 2 d. After usual workup, the products 18a and 21a or 18b and 21b were obtained (see Table 1). Compounds 18c or 18d were likewise obtained upon reacting 1a (or 1b) with an equimolar amount of benzoylmethylene(triphenyl)phosphorane under the same conditions as mentioned above and workup (data for 18c and 18d are listed in Table 1).
    • Typical Procedure for the Reaction of Isatoic Anhydrides 1a,b with Keto Ylides 16a,b A solution of acetylmethylene(triphenyl)phosphorane (4.9 mmol) and 1a (or 1b, 5.2 mmol) in 40 mL EtOAc containing benzoic acid was refluxed for 2 d. After usual workup, the products 18a and 21a or 18b and 21b were obtained (see Table 1). Compounds 18c or 18d were likewise obtained upon reacting 1a (or 1b) with an equimolar amount of benzoylmethylene(triphenyl)phosphorane under the same conditions as mentioned above and workup (data for 18c and 18d are listed in Table 1).
  • 27
    • 34249799704 scopus 로고    scopus 로고
    • Typical Procedure for the Reaction of Isatoic Anhydrides 1a,b with Phosphonium Salt 22 Diphenylmethylene(triphenyl)phosphonium bromide (22, 5.2 mmol) was added dropwise to a solution of abs. EtOH (50 mL) containing Na metal (0.4 g, The reaction mixture was stirred at r.t. for 1 h followed by addition of 1a (or 1b, 4.9 mmol, and then heated under reflux for 15 h. The product mixture was concentrated and diluted with a small amount of distilled H2O2, followed by solvent extraction (EtOAc, drying, and evaporation. The resulting residue was purified by chromatography on silica gel, gradient eluting using CHCl3-EtOAc to yield compounds 24a and 25a, or 24b and 25b, respectively. Compound 25a was obtained as pale yellow needles (130 mg, 16, mp 36-38°C from pentane, mp and mixed mp, as well as IR and mass spectral data were comparable to those of an available sample. Compound 24a w
    • 14

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