In:
Journal of Heterocyclic Chemistry, Wiley, Vol. 53, No. 5 ( 2016-09), p. 1469-1473
Abstract:
9‐Fluorenylmethoxycarbonyl was a good protecting group in the field of chemical industry. In the present paper, a new approach for the synthesis of oxadiazine insecticides indoxacarb used 9‐fluorenylmethoxycarbonyl as protected group, and triphosgene for chloroformylation. A convenient synthesis of 9‐fluorenylmethoxycarbonylhydrazine can be achieved by the nucleophilic substitution reaction of 9‐fluorenylmethyl chloroformate and hydrazine hydrate. 4a‐Methyl‐2‐(9‐fluorenylmethyl)‐7‐chloro‐indeno [1,2e][1,3,4] oxadia zine‐2,4a (3H,5H)‐dicarboxylate can be produced via ketone ‐hydrazine crosslink reaction and cyclization. A preparation of carbamic acid‐(chlorocarbonyl)‐[(4‐trifluoromethoxy) phenyl] me ester can be obtained by the chloroformylation of triphosgene. Finally, the deprotection of 9‐fluorenylmethoxy carbonyl and condensation with carbamic acid‐(chlorocarbonyl)‐[(4‐trifluoromethoxy) phenyl] me ester can afford indoxacarb in good yield. A new method for the synthesis of oxadiazine insecticides indoxacarb used 9‐fluorenylmethoxycarbonyl‐protected group to produce 9‐fluorenylmethoxycarbonylhydrazine, then through the ketone–hydrazine crosslink reaction, cyclization, deprotection, chloroformylation, and condensation in good yield.
Type of Medium:
Online Resource
ISSN:
0022-152X
,
1943-5193
Language:
English
Publisher:
Wiley
Publication Date:
2016
detail.hit.zdb_id:
2042274-X
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