The first general synthesis of N-substituted 1,2-benzisoxazolin-3-ones

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2295-2298

  Shi, Guo Qiang ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE; HYDROXAMIC ACID DERIVATIVE; ISOXAZOLINE DERIVATIVE; SALICYLHYDROXAMIC ACID; SALICYLIC ACID DERIVATIVE;

ACETYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DESICCATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034175712     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00164-7     Document Type: Article

References (9)

1. Boeshagen, H. Chem. Ber. 1967, 100, 594.
2. A small amount of N-alkylation product was obtained when a primary halide was used as the electrophile. However the desired N-alkylation product became essentially negligible when secondary halides was used. Similar results have been mentioned in a few patents. (a) Nagano, M.; Sakai, J.; Mizukai, M.; Nakamura, N.; Misaka, E.; Kobayashi, S.; Tomita, K. JP 79:54073772; Chem. Abstr. 91:211401. (b) Slawik, T.; Bien, I. PL 92:15571; Chem. Abstr. 94:244786.
3. A small amount of N-alkylation product was obtained when a primary halide was used as the electrophile. However the desired N-alkylation product became essentially negligible when secondary halides was used. Similar results have been mentioned in a few patents. (a) Nagano, M.; Sakai, J.; Mizukai, M.; Nakamura, N.; Misaka, E.; Kobayashi, S.; Tomita, K. JP 79:54073772; Chem. Abstr. 91:211401. (b) Slawik, T.; Bien, I. PL 92:15571; Chem. Abstr. 94:244786.
4. (a) Kalkote, U. R.; Goswami, D. D. Aust. J. Chem. 1977, 30, 1847.
5. (b) Sheradsky, T.; Avramovici-Grisaru, S. Tetrahedron Lett. 1978, 2325.
6. For a review of the Lossen rearrangement, see: Bauer, L.; Exner, O. Angew. Chem., Int. Ed. Engl. 1974, 13, 376.
7. Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380.
8. Friary, R.; Sunday, B. R. J. Heterocycl. Chem. 1979, 16, 1277.
9. 4: C, 67.69; H, 7.89; N, 4.39. Found: C, 67.55; H, 7.95; N, 4.33.