Molecular sieve (MS 4A) promoted cyclocondensation of hindered, aromatic nitrile oxides and cyclic diketones under mild conditions

Synlett

Volumn , Issue 11, 2003, Pages 1746-1748

  Matsuura, Tomoo ^a   Bode, Jeffrey W ^a   Hachisu, Yoshifumi ^a   Suzuki, Keisuke ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Condensation; Cycloadditions; Isoxazoles; Ketones; Molecular sieves

Indexed keywords

DIKETONE; ISOXAZOLE DERIVATIVE; MOLECULAR SIEVE 4A; NITRILE; OXIDE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; POLYMERIZATION; SYNTHESIS; TECHNIQUE;

EID: 0041910878     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41436     Document Type: Article

References (10)

1. (a) Bode, J. W.; Hachisu, Y.; Matsuura, T.; Suzuki, K. Tetrahedron Lett. 2003, 44, 3555.
2. (b) Bode, J. W.; Hachisu, Y.; Matsuura, T.; Suzuki, K. Org. Lett. 2003, 5, 391.
3. For a review of molecular sieve and zeolite promoted reactions, see: Sen, S. E.; Smith, S. M.; Sullivan, K. A. Tetrahedron 1999, 55, 12657.
4. The use of 4 Å MS as a base for the elimination of C-chloroximes to form nitrile oxides and subsequent cycloaddition with acrylates has been reported. However, under these conditions long reaction times (7-10 d) were necessary, see: Kim, J. N.; Ryu, E. K. Heterocycles 1990, 31, 1693.
5. 2O.
6. Thermal cycloadditions of 2-hydroxynaphthoquinone and nitrile oxides have been previously reported: Brahmeshwari, G.; Rao, V. R.; Rao, T. V. P. Indian J. Chem., Sect. B 1995, 34, 139.
7. Bode, J. W.; Suzuki, K. Org. Lett. 2003, 5, 394.
8. Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432.
9. Bode, J. W.; Suzuki, K. Tetrahedron Lett. 2003, 44, 3559.
10. For a Diels-Alder type cycloaddition reaction promoted by molecular sieves, see: Pindur, U.; Haber, M. Heterocycles 1991, 32, 1463.