ISOXAZOL-5(4H)-ONES - X-RAY CRYSTAL-STRUCTURES OF A 4-HYDROXYISOXAZOL-5(4H)-ONE AND A [4,4'-BIISOXAZOLE]-5(4H),5'(4'H)-DIONE FORMED BY OXYGEN OXIDATION OF 3-TERT-BUTYL-4-METHYLISOXAZOL-5(4H)-ONE

被引：9
作者：
BREHM, L
JOHANSEN, JS
KROGSGAARDLARSEN, P
机构：
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 16期
关键词：
D O I：
10.1039/p19920002059
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of ethyl (RS)-2,4,4-trimethyl-3-oxopentanoate 4 with hydroxylamine under basic conditions gave 5-tert-butyl-4-methylisoxazol-3-ol 5 and a tautomeric mixture of 3-tert-butyl-4-methylisoxazol-5 (2H)-one 6 and (RS)-3-tert-butyl-4-methylisoxazol-5(4H)-one 7. During the attempts to crystallize the inseparable mixture of tautomers 6 and 7 two other compounds, (RS)-3-tert-butyl-4-hydroxy-4-methylisoxazol-5 (4H)-one 8 and (RS,RS)-3,3'-di-tert-butyl-4,4'-dimethyl-[4,4'-biisoxazole]-5(4H), 5'(4'H)-dione 9, were progressively formed. The structures of compounds 8 and 9 were established by X-ray analyses. Compounds 8 and 9 are proposed to be formed by oxidation of compound 7 with oxygen, but the mechanisms underlying these two oxidative processes are unknown.
引用
收藏
页码：2059 / 2063
页数：5
相关论文
共 50 条
[21]   SYNTHESIS OF 5,6-DIHYDROPYRAN-3(4H)-ONE [J].
SATO, K ;
INOUE, S ;
TANAMI, T ;
OHASI, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (04) :1015-1018
[22]   Crystal structure and Hirshfeld surface analysis of (Z)-4-(4-hydroxybenzylidene)-3-methylisoxazol-5(4H)-one [J].
Zemamouche, Wissem ;
Laroun, Rima ;
Hamdouni, Noudjoud ;
Brihi, Ouarda ;
Boudjada, Ali ;
Debache, Abdelmadjid .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2018, 74 :926-+
[23]   Heavy hydrogen isotopes 4H and 5H [J].
Chulkov, LV .
NUCLEAR PHYSICS A, 2004, 734 :357-360
[24]   REACTION OF 4-METHYLENE-5(4H)-OXAZOLONES WITH DIAZOMETHANE [J].
ARENAL, I ;
BERNABE, M ;
ALVAREZ, EF ;
IZQUIERDO, ML ;
PENADES, S .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) :607-613
[25]   The diverse chemistry of oxazol-5-(4H)-ones [J].
Fisk, Jason S. ;
Mosey, Robert A. ;
Tepe, Jetze J. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (09) :1432-1440
[26]   4,4′-Butane-1,4-diylbis[3-ethyl-1H-1,2,4-triazol-5(4H)-one] and 4-hydroxy-3-n-propyl-1H-1,2,4-triazol-5(4H)-one [J].
Iskeleli, NO ;
Isik, S ;
Sancak, K ;
Samaz, S ;
Ünver, Y ;
Er, M .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 :O363-O365
[27]   An Efficient Synthesis of 4-Arylmethylidene-3-substituted-Isoxazol-5(4H)-ones in Aqueous Medium [J].
Chavan, Abhijit P. ;
Pinjari, Avinash B. ;
Mhaske, Pravin C. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) :1911-1915
[28]   FORMATION OF METHYL 5,6-DIHYDRO-1,3(4H)-THIAZINE-4-CARBOXYLATES FROM 4-ALLYL-1,3-THIAZOL-5(4H)-ONES [J].
JENNY, C ;
HEIMGARTNER, H .
HELVETICA CHIMICA ACTA, 1989, 72 (07) :1639-1646
[29]   Synthesis of symmetrical 2,2',4,4'-tetrasubstituted [4,4'-bithiazole]-5,5'(4H,4'H)-diones and their reactions with some nucleophiles [J].
Andersen, KK ;
Bray, DD ;
Kjaer, A ;
Lin, YH ;
Shoja, M .
ACTA CHEMICA SCANDINAVICA, 1997, 51 (10) :1000-1015
[30]   Efficient Synthesis of 4-Arylmethylene-3-methylisoxazol-5(4H)-one Derivatives Catalyzed by Malic Acid [J].
Tahmasabi, Sayed Zakaria ;
Kiyani, Hamzeh ;
Samimi, Heshmat Allah .
LETTERS IN ORGANIC CHEMISTRY, 2023, 20 (02) :167-174
12345