1969
DOI: 10.1002/prac.19693110512
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Über die Einwirkung von Enaminen auf Chinone. X. Lewissäurekatalysierte Umsetzungen von Aminofumarsäurediäthylester und N,N‐disubstituierten Aminomaleinsäuredimethylestern mit p‐Benzochinon

Abstract: Aminofumarsäurediäthylester reagiert mit p‐Benzochinon in Gegenwart äquimolarer Mengen Bortrifluorid unter thermodynamischer Kontrolle zum 3‐Amino‐6‐hydroxy‐4‐äthoxycarbonyl‐cumarin 2; die kinetisch kontrollierte Reaktion liefert das 3,6‐Dihydroxy‐4‐äthoxycarbonyl‐cumarin 3a. N,N‐disubstituierte Aminomaleinsäuredimethylester bilden mit p‐Benzochinon sowohl in Eisessiglösung ohne Katalysator als auch mit Bortrifluoridätherat in Diäthyläther das 2,3,6,7‐Tetramethoxycarbonyl‐benzo[1.2‐b; 4.5‐b′]difuran 5, bei den… Show more

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Cited by 10 publications
(4 citation statements)
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“…Here, it must be noted that the MDA displayed two carbonyl bands, which is in good accordance with literature. [47] A weak band corresponding to the allyl groups, at around 1647 cm −1 was detected in the spectra of all these monomers.…”
Section: Characterization Of the Synthesized Monomersmentioning
confidence: 91%
“…Here, it must be noted that the MDA displayed two carbonyl bands, which is in good accordance with literature. [47] A weak band corresponding to the allyl groups, at around 1647 cm −1 was detected in the spectra of all these monomers.…”
Section: Characterization Of the Synthesized Monomersmentioning
confidence: 91%
“…The attack of the solvent acetonitrile to the formed carbocations was also observed in other cases. 11,12 The product 2a was proved authentic by the reaction of 4-aminoresorcinol The formation of 2e can be interpreted in terms of the acetonitrile acting as a nucleophile via its nitrogen atom and attacking the formed cationic center at the C6-position, followed by cyclization with the formation of oxazolocoumarin derivative 2e. On the other hand, the lack of formation of 4 is due to the absence of water in the pure acetonitrile used.…”
Section: Figurementioning
confidence: 97%
“…A solution of /3-keto ester 48 (6.44 g, 1.81 mmol) in CH3OH (200 ml, anhydrous) was treated with triethylamine (1.82 g, 1.81 mmol) and allowed to stand at 25 °C for 7 days. Evaporation gives 6.44 g (100%) of cyclized /3-keto ester 50 as a foam, which was crystallized from benzene/hexane (1:2): mp 155-158 °C; NMR 7.25 (s, 5 H), 2.85 (s, 3 ), 1.48 (s, 9 H); ir 1715, 1664 (br) cm-1; MS m/e 357 (1), 301 (37), 284 (16), 283 (22), 257 (12), 256 (11), 255 (23), 59 (100). Anal: (C2iH27N04): C, , N. trans-1,6-Dioxo-2-methyl-4a-phenyldecahydroisoquinoline (51).…”
Section: Experimental Section10mentioning
confidence: 99%