Synthesis of pyrrolidine-substituted benzamides via iodocyclization of β-enaminoesters

Tetrahedron Letters

Volumn 48, Issue 36, 2007, Pages 6393-6396

  De Oliveira, Eliseu O ^a,b   Brandt, Carlos A ^c   Da Silveira, Maria A B ^a   Glennon, Richard A ^b  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^c INSTITUTO BUTANTAN   (Brazil)

Author keywords

Enaminoesters; 2 Pyrrolines; Benzamides; Iodocyclization; Pyrrolidines

Indexed keywords

BENZAMIDE; BENZOIC ACID; BETA ENAMINOESTER; ESTER; IODIDE; PYRROLIDINE DERIVATIVE; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; HALOGENATION; HYDROGENATION; REACTION ANALYSIS; REDUCTION; REPRODUCIBILITY; SYNTHESIS;

EID: 34547684396     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.166     Document Type: Article

References (21)

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5. 2
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15. 3): δ 11.4, 24.8, 31.2, 39.1, 41.3, 50.1, 56.3, 62.1, 78.1, 112.9, 122.2, 126.8, 131.9, 132.6, 155.9, 164.5, 164.9, 169.6.
16. 13C NMR data. See Table 1 for yields and melting points.
17. 2-MeOH 9:1) to give a light yellow oil. 11a (R = Et): yield 88%; 11b (R = Bn): yield 90%; 12: yield 70%.
18. f's in hexanes-AcOEt 4:1.
19. f's in hexanes-AcOEt 4:1.
20. f's in hexanes-AcOEt 4:1.
21. EDC: N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride; DBU: 1,8-Diazabicyclo[5.4.0]undec-7-ene; DMF: N,N-Dimethylformamide.