REACTIVITY OF 2-METHYL-4-(1-PYRROLIDINYL)-2H-1,2-BENZOTHIAZINE 1,1-DIOXIDE TOWARDS PARA-TOLUENESULFONYL AZIDE

被引:3
作者
CONSONNI, R [1 ]
CROCE, PD [1 ]
FERRACCIOLI, R [1 ]
机构
[1] CNR,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
关键词
D O I
10.1002/jhet.5570270260
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 2‐methyl‐2H‐1,2‐benzothiazin‐4‐(3H)‐one 1,1 dioxide (2), obtained according to a new, one‐pot method, is transformed into the pyrrolidino enamine 3. Reaction of p‐toluenesulphonyl azide with 3 gives, via an unstable triazoline adduct which loses nitrogen, the two isomeric tosylamino derivatives 4 and 5. The structures have been assigned by exhaustive nmr analysis and some aspects on their formation and chemical behaviour are discussed. Copyright © 1990 Journal of Heterocyclic Chemistry
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页码:427 / 431
页数:5
相关论文
共 20 条
[1]   RING-EXPANSION OF 3-BROMOALKYL-1,2-BENZISOTHIAZOLE 1,1-DIOXIDES TO (2H)-1,2-BENZOTHIAZIN-4(3H)-ONE 1,1-DIOXIDES [J].
ABRAMOVITCH, RA ;
MORE, KM ;
SHINKAI, I ;
SRINIVASAN, PC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (19) :771-772
[2]   TWO-DIMENSIONAL EXCHANGE DIFFERENCE SPECTROSCOPY APPLICATIONS TO INDIRECT OBSERVATION OF QUADRUPOLAR RELAXATION [J].
BODENHAUSEN, G ;
ERNST, RR .
MOLECULAR PHYSICS, 1982, 47 (02) :319-328
[3]  
CROCE PD, 1986, J CHEM RES-S, P150
[4]   SYNTHESIS, STRUCTURE, AND REACTIVITY TO NUCLEOPHILES OF 3-BENZYLIDENE AND 3-ETHYLIDENE-2,3-DIHYDRO-2-METHYL-1,2-BENZOTHIAZIN-4-ONE 1,1-DIOXIDES [J].
CROCE, PD ;
DELMONACO, D ;
LAROSA, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (02) :299-302
[5]   UPSILON-TRIAZOLINES .6. REARRANGEMENT OF TRIAZOLINES FROM 2-SUBSTITUTED-1-ARYL-1-AMINO-ETHYLENES AND 1-HETEROARYL-1-AMINO-ETHYLENES AND TOSYLAZIDE [J].
CROCE, PD ;
STRADI, R .
TETRAHEDRON, 1977, 33 (08) :865-867
[6]   HALOGENOLYSIS OF METHYL GLYCYRRHETATE WITH LITHIUM IODIDE-DIMETHYLFORMAMIDE [J].
DEAN, PDG .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (NOV) :6655-&
[7]   COMBINED SUPPRESSION OF DIAGONAL PEAKS AND T1 RIDGES IN TWO-DIMENSIONAL NUCLEAR OVERHAUSER ENHANCEMENT SPECTRA [J].
DENK, W ;
WAGNER, G ;
RANCE, M ;
WUTHRICH, K .
JOURNAL OF MAGNETIC RESONANCE, 1985, 62 (02) :350-355
[8]   USE OF ACYL MIGRATION IN SEPARATING DIASTEREOISOMERIC AMINO ALCOHOLS [J].
FODOR, G ;
BRUCKNER, V ;
KISS, J ;
OHEGYI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1949, 14 (03) :337-345
[9]  
Fusco R., 1961, GAZZ CHIM ITAL, V91, P849
[10]  
HALLEUX Y, 1970, J CHEM SOC C, P881