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Synlett

Volumn , Issue 12, 2007, Pages 1921-1924

Efficient oxidative conversion of aldehydes to 2-substituted oxazolines and oxazines using (diacetoxyiodo)benzene

(3) Karade, Nandkishor N a Tiwari, Girdharilal B a Gampawar, Sumit V a

a SWAMI RAMANAND TEERTH MARATHWADA UNIVERSITY (India)

Author keywords

Aldehydes; Hypervalent iodine; Oxazines; Oxazolines; Oxidation

Indexed keywords

(DIACETOXYIODO)BENZENE; 2 (3,4,5 TRIMETHOXYPHENYL) 4,5 DIHYDROOXAZOLE; 2 (4 CHLOROPHENYL) 4,5 DIHYDROOXAZOLE; 2 (4 METHOXYPHENYL) 4,5 DIHYDROOXAZOLE; 2 (4 METHOXYPHENYL) 5,6 DIHYDRO 4H [1,3]OXAZINE; 2 (4 NITROPHENYL) 4,5 DIHYDROOXAZOLE; 2 (4 NITROPHENYL) 5,6 DIHYDRO 4H [1,3]OXAZINE; 2 (4 TOLYL) 4,5 DIHYDROOXAZOLE; 4 ETHYL 4,5 DIHYDRO 2 (4METHOXYPHENYL)OXAZOLE; ALDEHYDE DERIVATIVE; AMINOPROPANOL; BENZENE DERIVATIVE; OXAZINE DERIVATIVE; OXAZOLINE DERIVATIVE; PROPANOLAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; OXIDATION; SUBSTITUTION REACTION;

EID: 34547615981 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-982571 Document Type: Article

Times cited : (49)

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- Typical Experimental Procedure A mixture of an aldehyde (1.0 mmol) and an appropriate 2-amino alcohol (1.0 mmol) was stirred for 4 h at r.t, Diacetoxyiodo)benzene (1.2 mmol) was then added to the above mixture and the resulting reaction mixture was again subjected for stirring for another 3-6 h. The progress of the reaction was monitored by TLC. After the completion of the reaction, H2O (15 mL) was added and the mixture extracted with CH2Cl2 (2 x 15 mL, The combined organic extracts were dried over anhyd Na2SO4, concentrated in vacuo, and chromatographed to give 2-substituted oxazolines/oxazines. Spectroscopic Data of Selected Products 2-(4-Nitrophenyl)-4,5-dihydrooxazole Mp 157-159°C. IR (KBr, 3028, 2971, 2894, 1649, 1602, 1528, 1464, 1349, 1268, 1092, 952, 861, 710 cm-1. 1H NMR (CDCl3, δ, 4.12 (t, J, 9.6 Hz, 2 H, 4.50 (t, J, 9.6 Hz, 2 H, 8.14 d, J
- 3): δ = 1.99 (quin, J = 5.8 Hz, 2 H), 3.66 (t, J = 5.6 Hz, 2 H), 4.37 (t, J = 5.6 Hz, 2 H), 8.07 (d, J = 9.2 Hz, 2 H), 8.22 (d, J = 9.3 Hz, 2 H). LCMS [M + 1]: m/z = 207.

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- 3 (10 mL) was independently carried out at r.t. stirring for another 3 h. After usual reaction workup, the formation of 4,5-dihydro-4,4-dimethyl-2- styryloxazole was realized in 38% yield.
- 3 (10 mL) was independently carried out at r.t. stirring for another 3 h. After usual reaction workup, the formation of 4,5-dihydro-4,4-dimethyl-2- styryloxazole was realized in 38% yield.

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