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Volumn , Issue 7, 2007, Pages 1085-1090

Three-component reactions of α- and β-bromo aldehydes with amides and dienophiles - An easy way to versatile 1-amido-2-cyclo hexenes

Author keywords

Amides; Diels Alder reaction; Dienophiles; Halogenated aldehydes; Multicomponent reaction

Indexed keywords

1 AMIDO 2 CYCLOHEXENE DERIVATIVE; ALDEHYDE DERIVATIVE; AMIDE; CYCLOHEXENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34248204132     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-973898     Document Type: Article
Times cited : (7)

References (41)
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    • The crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 635328 6
    • The crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 635328 (6).
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    • rac-N-(5-Bromo-2-methyl-1,3-dioxo-2,3,3a,4,7, 7a-hexahydro-1H-isoindol-4-yl)-4-methoxybenzamide(5) 4-Methoxybenzamide (152 mg, 1.00 mmol) was filled in a CEM pressure tube (10 mL, then toluene (2 mL, α-bromocrotonaldehyde (2.00 mmol, 298 mg, and N-methyl-maleimide (1.50 mmol, 167 mg) were added. The reaction vessel was sealed and the mixture was subject to microwave irradiation (max. 50 W, 2450 MHz) under stirring at 150°C for 20 min. After cooling, compound 5 precipitated from the reaction mixture. It was obtained as a colorless solid (84% yield) after washing with CH2Cl2. Further purification was not necessary. The assignment of the NMR signals was carried out according to the numbering given in Table 2. Mp 257°C. 1H NMR (500 MHz, DMSO-d6, δ, 8.31 (d, 3J9,4, 9.0 Hz, 1 H, H-9, 7.75 (m, 2 H, H-12, 7.05 (m, 2 H, H-13, 6.35 ddd
    • +.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.