Concurrent α-iodination and N-arylation of cyclic β-enaminones

Synlett

Volumn , Issue 2, 2010, Pages 231-234

  Chen, Yan ^a   Ju, Tong ^a   Wang, Junwei ^a   Yu, Wenquan ^a   Du, Yunfei ^a   Zhao, Kang ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

iodo enaminones; iodination; 3 aminocyclohex 2 enones; PIDA; Polyvalent iodine compounds

Indexed keywords

3 AMINOCYCLOHEX 2 ENONE; ALPHA IODO ENAMINONE; CYCLIC BETA ENAMINONE; IODINE DERIVATIVE; PHENYLIODINE DIACETATE; POLYVALENT IODINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; IODINATION; ORGANIC CHEMISTRY; OXIDATION; X RAY CRYSTALLOGRAPHY;

EID: 75749127791     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219164     Document Type: Article

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45. General Procedure for a-Iodination and N-Arylation of b-Enaminones To a solution of substrate 1 (1.0 mmol) in dried DCE (10 mL) was added dropwise a solution of aryliodine diacetate 2 (1.3 mmol) in dried DCE (10 mL) at 60 C under nitrogen atmosphere. After the addition, the reaction mixture was stirred at this temperature until the conversion was complete as indicated by TLC. Then the mixture was cooled to r.t., treated with sat. aq NaHCO3 (40 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic layer was dried over Na2SO4 and evaporated under reduced pressure to remove the solvent. The residue was purified by column chromatography using a mixture of PE and EtOAc as eluent to afford the product. Compound 3a: yellow solid, mp 106108 C. 1H NMR (500 MHz, CDCl3): d = 7.32 (t, J = 7.9 Hz, 4 H), 7.14 (t, J = 7.4 Hz, 2 H), 7.02 (d, J = 7.7 Hz, 4 H), 2.752.65 (m, 2 H), 2.58 (t, J = 6.0 Hz, 2 H), 2.041.91 (m, 2 H). 13C NMR (100 MHz, CDCl3): d = 193.09, 166.95, 145.20, 129.52, 125.45, 125.22, 95.80, 37.54, 34.04, 21.38. ESI-LRMS: m/z = 390.2 [M + H+]. Compound 5a: yellow solid, mp 102104 C. 1H NMR (400 MHz, DMSO): d = 7.51 (dd, J = 4.8, 2.5 Hz, 3 H), 7.35 (dd, J = 7.7, 1.9 Hz, 2 H), 2.43 (s, 3 H), 2.35 (s, 3 H), 2.22 (s, 3 H). ESI-LRMS: m/z = 271.9 [M + K+]. The spectroscopic data for all the new compounds could be found in the Supporting Information.