- OXATHIAZINE DERIVATIVES SUBSTITUTED WITH CARBOCYCLES OR HETEROCYCLES, METHOD FOR PRODUCING SAME, DRUGS CONTAINING SAID COMPOUNDS, AND USE THEREOF
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The invention relates to the compounds of formula (I) and physiologically acceptable salts thereof. The compounds are suitable, e.g., for treating hyperglycemia.
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Paragraph 0405; 0406
(2014/02/15)
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- 2-Dienylphenacyloxazolones and an intramolecular Diels-Alder approach to the A-B-C ring system of phenanthridone alkaloids
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A general route to the A-B-C ring system of phenanthridone alkaloids is available by acylation of 2-oxa-zolone with a 2-butadienylbenzoic acid derivative, followed by an intramolecular Diels-Alder reaction and hydrolysis.
- Gaenzler, Faith Corbo,Guo, Chen (Lisa),Zhang, Yun-Wei,Azab, Mohammad E.,Salem, Mounir A.I.,Fan, Dong Ping,Smith, Michael B.
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scheme or table
p. 8781 - 8785
(2009/12/26)
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- A dichlorination-reductive-dechlorination route to N-acetyl-2-oxazolone
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We have shown that sulfuryl chloride is an efficient reagent for the conversion of 2-oxazolidinone into the dichloro derivative, N-acetyl-4,5- dichloro-2-oxazolidinone. Subsequent Zn/AcOH reductive dehalogenation of this trans-dichloride gives N-acetyl-2-oxazolone. The dichloride was previously reported as an undesired side product in the preparation of N-acetyl-2-oxazolone from the monochloro oxazolidinone. In our hands, the dichloride is a key intermediate in a new synthesis of 2-oxazolone, that avoids the use of chlorine gas. Georg Thieme Verlag Stuttgart.
- Gaenzler, Faith Corbo,Smith, Michael B.
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p. 1299 - 1301
(2008/02/08)
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- A CONVENIENT PREPARATION OF 3H-1,3-OXAZOL-2-ONE AND ITS N-FORMYL DERIVATIVE
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The electrochemical hydroxylation of 1,3-oxazolidin-2-one to 4-hydroxy-1,3-oxazolidin-2-one is reported; a substantial size product is the symmetrical ether derived from the hydroxycompound.An improved synthesis of 3H-1,3-oxazol-2-one has been developed; nothing more is involved than boiling the readily available 4-methoxy-1,3-oxazolidin-2-one with an excess of acetic acid and one equivalent of acetic anhydride, evaporation of the solvents and recrystallization of the residue.The mechanism of the reaction is discussed.In a reinvestigation of the known conversion, by acetic anhydride, of 4-methoxy-1,3-oxazolidin-2-one to N-acetyl-1,3-oxazol-2-one, we have uncovered the formation of two 3,4'-bioxazole side products , especially in the presence of added acids.We have found that N-formyl-1,3-oxazol-2-one can be made in good yield by treatment of 3H-1,3-oxazol-2-one with a mixture of formic acid and acetic anhydride ("acetic formic anhydride") in the presence of 4-(N,N-dimethylamino)pyridine; the formation of an intermediate phosphonate derived from 3H-1,3-oxazol-2-one, as described in the literature synthesis of N-formyl-1,3-oxazolone, is superfluous.
- Tavernier, Dirk,Damme, Sabine van,Ricquier, Patrick,Anteunis, Marc J. O.
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p. 859 - 866
(2007/10/02)
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- A NEW SYNTHESIS OF 2-OXAZOLONES
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2-oxazolones were synthesized from 2-oxazolidinones utilizing anodic oxidation as the key step.
- Wang, Pen-Chung
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p. 2237 - 2238
(2007/10/02)
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- Highly Stereo- and Regioselective Formation of 2-Oxazolone Telomers, Potential Synthetic Intermediates for Amino Sugars
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Free radical initiated reaction of 3-acyl-2-oxazolones proceeds smoothly in polyhalomethanes, which function as telogens, to give type 3 telomers of synthetic potential with high regio- and stereoselectivity, while the 3-alkyl derivatives failed to give such polyfunctional products.This particular telomerization can be controlled exclusively in the trans ''head-to-tail'' addition mode, as elucidated by 1H and 13C NMR and X-ray analysis of the products.Thus, the 3-benzoyl heterocycle 7 gave trans-4-chloro-5-(trichloromethyl)-2-oxazolidone (8) as a sole 1:1 adduct andtwo trans isomers of 4'-chloro-5-(trichloromethyl)-2,2'-dione (9a,b) as 2:1 telomers.Some characteristic reactions of the telomers are described.
- Kunieda, Takehisa,Abe, Yoshihiro,Iitaka, Yoichi,Hirobe, Masaaki
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p. 4291 - 4297
(2007/10/02)
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- A NEW REAGENT FOR ACTIVATING CARBOXYL GROUPS: DIPHENYL 2-OXO-3-OXAZOLINYLPHOSPHONATE
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Diphenyl 2-oxo-3-oxazolinylphosphonate serves as a carboxyl-activating reagent to permit a direct preparation of versatile intermediate, 3-acyl-2-oxazolones or a one-step formation of amides from carboxylic acids.
- Kunieda, Takehisa,Abe, Yoshihiro,Higuchi, Tsunehiko,Hirobe, Masaaki
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p. 1257 - 1258
(2007/10/02)
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