N-SULFONYLAMIDINES .4. INTRAMOLECULAR CYCLIZATION OF N-SULFONYLAMIDINES OF 2-OXOACIDS - A NEW SYNTHESIS OF 3-AMINOISOTHIAZOLE S,S-DIOXIDES

被引：16

作者：

CLERICI, F

MARAZZI, G

TAGLIETTI, M

机构：

[1] IST RICERCHE SIGMA TAU,MILAN,ITALY

[2] UNIV MILAN,FAC FARM,IST CHIM ORGAN,I-20133 MILAN,ITALY

来源：

TETRAHEDRON | 1992年 / 48卷 / 15期

关键词：

N-SULFONYLAMIDINES; 3-AMINO-ISOTHIAZOLE S; S-DIOXIDES; INTRAMOLECULAR CYCLIZATION; ISOTHIAZOLINE S; CONFIGURATION;

D O I：

10.1016/S0040-4020(01)92260-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-alkylsulfonylamidines of alpha-ketoacids 3 bearing both a carbonyl group and at least one H-atom near to the SO2 group give easily an intramolecular ring-closure reaction by action of potassium t-butoxide producing the 3-amino-4,5-dihydro-4-hydroxy-isothiazole S,S-dioxides 4. Compounds 4 are transformed by thionyl chloride into the corresponding chloro-derivatives 5 which in turn are dehydrochlorinated by potassium carbonate to substituted 3-amino-isothiazole S,S-dioxides 6.

引用

页码：3227 / 3238

页数：12

共 50 条

[21] CYCLIC ARYLENEAZACHALCOGENENES .8. REGIOSELECTIVITY OF FLUORIDE ION-INDUCED INTRAMOLECULAR NUCLEOPHILIC CYCLIZATION OF HEPTAFLUORONAPHTHYL SULFUR DIIMIDES 2-NF(F)-N=S=N-SIME(3) AND 2-NF(F)S-N=S=N-S1ME(3)
BAGRYANSKAYA, IY
GATILOV, YV
MILLER, AO
SHAKIROV, MM
ZIBAREV, AV
HETEROATOM CHEMISTRY, 1994, 5 (5-6) : 561 - 565
[22] A facile synthesis of N,N′-oligomethylenebis(4,5-dihydrofuran-3-carboxamide)s using manganese(III)-based radical cyclization of N,N′-oligomethylenebis(3-oxobutanamide)s with 1,1-diarylethenes
Chowdhury, FA
Nishino, H
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (07) : 1337 - 1344
[23] Synthesis and structure of the group 12 pyrimidinethiolate complexes ∞3[Zn(S-2-N2C4H3)2], ∞2[Cd(S-2-N2C4H3)2], [Hg(S-2-N2C4H3)2] and [Cd(S-2-N2C4H3)2(tmeda)]
Eichhöfer, A
Buth, G
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2005, (20) : 4160 - 4167
[24] (TRIFLUOROMETHYLTHIOAMINO)BORANES .4. PREPARATION AND PROPERTIES OF [(CF3S)2N]NBX3-N WITH N = 3, N = 2, X = CL, BR, N3, AND N = 1, X = N3
HAAS, A
WILLERTPORADA, M
CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (04): : 1463 - 1475
[25] Synthesis and metal-ion binding properties of new N2S4- and N2S5-donor macrocycles
Hakan Alp
Zekeriya Biyiklioğlu
Gülsev Dilber
ÜmmÜhan Ocak
Aysel Marap
Halit Kantekin
Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2007, 58 : 283 - 288
[26] Synthesis and metal-ion binding properties of new N2S4- and N2S5-donor macrocycles
Alp, Hakan
Biyikliojlu, Zekeriya
Dilber, Gulsev
Ocak, Ummuhan
Marap, Aysel
Kantekin, Halit
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2007, 58 (3-4) : 283 - 288
[27] Synthesis of meso-thienyl-and meso-furyl N2S3 sapphyrins and N2S4 rubyrins
Rai, Smita
Mangalampalli, Ravikanth
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2007, 11 (11-12) : 784 - 794
[28] Stereoselective synthesis of N-benzyl (2S,3S,4S)-3-hydroxy-4-methylproline
Hiremath, Mahanthaswamy
Kumar, Yalechakanahalli C. Sunil
Umashankara, Muddegowda
Sandhya, Nagarakere C.
Chandrappa, Siddapa
Kumar, Chottanahalli S. Pavan
Mantelingu, Kempegowda
Rangappa, Kanchugarakoppalu S.
TETRAHEDRON-ASYMMETRY, 2016, 27 (06) : 261 - 267
[29] A NEW SAMARIUM NITRIDE SULFIDE - SM4N2S3
LISSNER, F
SCHLEID, T
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1994, 620 (11): : 2003 - 2007
[30] SYNTHESIS AND REACTIONS OF ALKALI-METAL DERIVATIVES OF THE PH(4)P(2)N(4)S(2)(2-) DIANION - X-RAY STRUCTURE OF CP-ASTERISK-RH(ETA(3)-PH(4)P(2)N(4)S(2)-N,S,S')
CHIVERS, T
EDWARDS, M
GAO, XL
HILTS, RW
PARVEZ, M
VOLLMERHAUS, R
INORGANIC CHEMISTRY, 1995, 34 (20) : 5037 - 5041

← 1 2 3 4 5 →