1,3-Dipolar cycloaddition of nitrile-N-oxides with 3,5-di-tert-butyl-1,2-benzoquinone: Facile formation of spiro-1,3-dioxazoles

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5623-5626

  Nair, Vijay ^a   Radhakrishnan, K V ^a   Nair, Anilkumar G ^a   Bhadbhade, Mohan M ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605894     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01172-0     Document Type: Article

References (26)

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22. 21 (0.250 g, 1.50 mmol) in benzene (10 mL) was added to a solution of 3,5-di-tert/-butyl-1,2-benzoquinone (0.220 g, 1.0 mmol) and triethyl amine (0.152 g, 1.5 mmol) in benzene at room temperature and stirred. When the reaction was complete (as indicated by TLC,30 min.), the reaction mixture was filtered to remove triethyl amine hydrochloride and the solvent was evaporated in vacuo. The residue obtained was chromatographed on a silica gel column. Elution with 1% and 2% ethyl acetate in hexane afforded 3 (60% m.p 116-118°C) and 4 (20% m.p 120-122°C) as yellow crystalline solids.
23. 3 (δ): 193.41,163.79,159.76 151.17,142.2129.36,127.03,125.27,119.63,115.39,104,29,36.93,35.91,29.92,27.89, 21.53 ppm. CHN analysis: Found C-74.4362 %, H-7.69411 %, N-3.72221 % (calculated-74.76 %, H-7.7%, N-3.96 %)
24. 3, orange yellow crystals, 0.32× 0.28×0.16 mm, monoclinic, space group p 21/c, unit cell dimensions: a = 18.207(7)°A,α = 90 deg, b =9.921(5)°A, β =106.03(4) deg, c = 23.42(11)°A, γ =90 deg. RI = 0.960, WR2 = 0.1572, Z = 8, density = 1.155 mg/ m-3, F(000) =1520, n=0.076 mm-1.
25. 25. Sheldrick, G.M.(1985) SHELXS-86. Program for the solution of crystal structures, University of Gottingen, Germany.
26. 26. Sheldrick, G.M.( 1993) SHELXL-93. Program for the refinement of crystal structures, University of Gottingen, Germany.