Conversion of 3-aryl-5-phenyl-2(3H)-furanones into 3(2H)-isothiazolone derivatives

被引：20

作者：

Derbala, HA ^{[1
]}

Hamad, ASS ^{[1
]}

El Said, WA ^{[1
]}

Hashem, AI ^{[1
]}

机构：

[1] Ain Shams Univ, Fac Sci, Dept Chem, Cairo, Egypt

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2001年 / 175卷

关键词：

2(3H)-furanones; N-benzylamides; isomerization; 3(2H)-isothiazolones; debenzoylation;

D O I：

10.1080/10426500108040263

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Upon heating 3-aryl-5-phenyl-2(3H)-furanones (1a-c) with benzylamine at 100 degreesC in the absence of solvents, ring opening occurred with the formation of the corresponding N-benzy-lamides (3a-c). When the latter compounds (3a-c) were allowed to react with thionyl chloride at room temperature, the corresponding isothiazolones (4a-c) were obtained. Treatment of the isothiazolones (4a-c) with sodium hydroxide in benzene at room temperature affected debenzoylation to give the corresponding 2-benzyl-4-aryl-3(2H)-isothiazolones (5a-c).

引用

页码：153 / 162

页数：10

共 50 条

[21] SYNTHESIS OF 3(2H)-FURANONES AND 3-METHOXYFURANES
MEISTER, C
SCHARF, HD
SYNTHESIS-STUTTGART, 1981, (09): : 737 - 739
[22] PHOTOCHEMISTRY OF 5-ARYL-2(3H)-FURANONES - A NEW ROUTE TO THE SYNTHESIS OF CHROMONES
MARTINEZUTRILLA, R
MIRANDA, MA
TETRAHEDRON, 1981, 37 (11) : 2111 - 2114
[23] ETHYL 5-SUBSTITUTED-3-ISOXAZOLECARBOXYLATES AS STARTING MATERIALS FOR A CONVENIENT ROUTE TO 3(2H)FURANONES AND 3(2H)IMINOFURANES
BARALDI, PG
BARCO, A
BENETTI, S
MANFREDINI, S
POLLINI, GP
SIMONI, D
TETRAHEDRON LETTERS, 1984, 25 (38) : 4313 - 4316
[24] REACTIVITY OF 5-METHYL-3(2H)-FURANONES TOWARD SCHIFF-BASES - SYNTHESIS OF 5-STYRYL-3(2H)-FURANONE DERIVATIVES
CHANTEGREL, B
GELIN, S
SYNTHESIS-STUTTGART, 1981, (01): : 45 - 47
[25] Thermal Decomposition of 2(3H) and 2(5H) Furanones: Theoretical Aspects
Wuermel, Judith
Simmie, John M.
Losty, Michelle M.
McKenna, Cathal D.
JOURNAL OF PHYSICAL CHEMISTRY A, 2015, 119 (26): : 6919 - 6927
[26] SYNTHESIS AND CHARACTERIZATIONS OF RETINOIDAL 3(2H)-FURANONES
ITO, M
OHNO, M
TAKANO, E
ODA, Y
TSUKIDA, K
HETEROCYCLES, 1979, 12 (04) : 505 - 509
[27] Conversion of 2(3H)-furanones bearing indole nuclei into novel amide, pyrrolone, and imidazole derivatives
Elgazwy, ASSH
Zaky, HT
Mohamed, MI
Ahmed, HM
Kandile, NG
HETEROATOM CHEMISTRY, 2003, 14 (05) : 434 - 442
[28] A NEW APPROACH TO POLYFUNCTIONAL 3(2H)-FURANONES
ANTONIOLETTI, R
BONADIES, F
PRENCIPE, T
SCETTRI, A
GAZZETTA CHIMICA ITALIANA, 1988, 118 (09): : 629 - 632
[29] 3(2H)ISOTHIAZOLONE, A NEW CLASS OF ANTIFOULING TOXICANT
MILLER, GA
LOVEGROVE, T
JOURNAL OF COATINGS TECHNOLOGY, 1980, 52 (661): : 69 - 72
[30] Synthesis of 5-Aryl-3(2H)-furanones Using Intramolecular Cyclization of Sulfonium Salts
Inagaki, Sho
Saito, Kai
Suto, Soichiro
Aihara, Hiromi
Sugawara, Aoi
Tamura, Satoru
Kawano, Tomikazu
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (22): : 13834 - 13846

← 1 2 3 4 5 →