Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1997-11-14
1999-04-06
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
544 96, C07D26508, C07D295125
Patent
active
058920307
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP96/01954, filed May 9, 1996.
The invention relates to a new process for the preparation of 5,6-dihydro-1,3-oxazines, some of which are new, to new 5,6-dihydro-1,3-oxazines, and to new intermediates for their preparation and their use for combating animal pests.
It is known that 5,6-dihydro-1,3-oxazines are obtained when aminoalcohols of the formula (A) are reacted with carboxylic acids of the formula (B) in the presence of a dehydrating agent in accordance with the following equation: ##STR3## (cf., in this context, EP-A 0 635 500 and WO-A 94/14783).
Furthermore, it is known that 5,6-dihydro-1,3-oxazines are obtained when amino-alcohols of the formula (A) are first reacted with acid chlorides of the formula (C) and the resulting amidoalcohols of the formula (D) are subsequently cyclized with dehydrating agent in accordance with the following equation: ##STR4## (cf., in this context, EP-A 0 635 500 and WO-A 94/14783).
Furthermore, it is known that 5,6-dihydro-1,3-oxazines are obtained when amino-alcohols of the formula (E) are reacted with nitrites of the formula (F) in the presence of rhodium complexes, if appropriate with an addition of diphosphines, in accordance with the following equation: ##STR5## (cf., in this context, JP-A 06 298 746).
However, the product yields which can be obtained in these known synthetic methods are not satisfactory, in particular with a view to the overall process, i.e. including the preparation of the aminoalcohols of the formulae (A) and (E) required as starting substances: The aminoalcohols can only be obtained in unsatisfactory yields via a plurality of steps and using expensive precursors and reducing agents, additional technical problems occurring due to substantial amounts of reducing agents and solvents and due to the fact that some processes have to be carried out under inert gas.
It has now been found that 5,6-dihydro-1,3-oxazines of the formula (I) ##STR6## in which A represents substituted phenyl, or represents in each case optionally substituted naphthyl, pyridyl, thienyl or pyrazolyl, and alkenyl, optionally substituted cycloalkyl, or in each case optionally substituted phenyl, phenylalkyl, phenylalkenyl, phenoxyalkyl, phenylthioalkyl, pyridyl or 2- or 3-pyrrolyl ##STR7## in which A and B have the abovementioned meanings and alkyl, or together with the N atom to which they are bonded represent an optionally substituted heterocycle catalyst, if appropriate in the presence of a diluent.
Surprisingly, the process according to the invention allows 5,6-dihydro-1,3-oxazines of the formula (I) to be obtained in good yields and in high purity, even though no noticeable reaction was to be expected due to the low reactivity of ethylene.
Thus, the reaction according to the invention has the advantage of being easier to carry out while simultaneously improving the yield, in particular with a view to the overall process, i.e. taking into consideration the preparation of the precursors (cf. also the preparation examples).
Formula (I) provides a general definition of the compounds to be prepared according to the invention. Preferred substituents or ranges of the radicals listed in the formulae mentioned hereinabove and hereinbelow are illustrated in the following text. by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -halogenoalkyl, C.sub.1 -C.sub.6 -halogenoalkoxy, C.sub.1 -C.sub.6 -halogenoalkylthio, nitro, cyano or by phenyl which is optionally monosubstituted to pentasubstituted by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -halogenoalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -halogenoalkoxy, C.sub.1 -C.sub.6 -alkylthio and C.sub.1 -C.sub.6 -halogenoalkylthio, trisubstituted by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -halogenoalkoxy,
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Bayer Aktiengesellschaft
Raymond Richard L.
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