A ONE-STEP SYNTHESIS OF 2,3-DIHYDRO-1,4-BENZOTHIAZINES AND PHENOTHIAZINES FROM 1,3-THIAZOLIDINE DERIVATIVES OF CYCLOHEXANONES

被引：4

作者：

CAPUTO, R

FERRERI, C

LONGOBARDO, L

MASTROIANNI, D

PALUMBO, G

PEDATELLA, S

机构：

[1] Dipartimento di Chimica Organica e Biologica, Università di Napoli Federico II -, 1-80134 Napoli, Via Mezzocannone

来源：

HETEROCYCLES | 1993年 / 36卷 / 07期

关键词：

D O I：

10.3987/COM-93-6379

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Acetyl-1,3-thiazolidine derivatives of cyclohexanones, when treated with a threefold excess N-bromosuccinimide in anhydrous chloroform at room temperature, smoothly afford N-acetyl-2,3-dihydro-1,4-benzothiazines. This represents the first general route to such heterocyclic system in one step from aliphatic precursors. The synthesis of optically active N-acetyl-2,3-dihydro-1,4-benzothiazines is also reported.

引用

页码：1641 / 1644

页数：4

共 7 条

[1] SOME DERIVATIVES OF PHENOTHIAZINE [J].

BURGER, A ;

CLEMENTS, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (07) :1113-1116

[2] REACTIVITY OF ETHANEDIYL S,S-ACETALS .3. RING AROMATIZATION IN CYCLOHEXANONE DERIVATIVES - A NOVELTY SYNTHESIS OF 1,4-BENZODITHIANS [J].

CAPUTO, R ;

FERRERI, C ;

PALUMBO, G ;

RUSSO, F .

TETRAHEDRON, 1991, 47 (24) :4187-4194

[3] THE REACTION OF ETHANEDIYL S,S-ACETALS WITH HALOGENS [J].

CAPUTO, R ;

FERRERI, C ;

PALUMBO, G ;

CAPOZZI, G .

TETRAHEDRON, 1986, 42 (08) :2369-2376

[4]

CAPUTO R, 1993, HETEROCYCLES, V36, P281

[5] STUDIES IN ORGANIC SULPHUR COMPOUNDS .17. SYNTHESIS OF PREVIOUSLY INACCESSIBLE ACYLATED ENAMINES BY DESULPHURISATION OF THIAZOLIDINES [J].

CROSSLEY, NS ;

DJERASSI, C ;

KIELCZEW.MA .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (NOV) :6253-&

[6] 10-AMINOACYLPHENOTHIAZINES .2. AMINOBUTYRYL DERIVATIVES [J].

DAHLBOM, R ;

EKSTRAND, T .

ACTA CHEMICA SCANDINAVICA, 1952, 6 (08) :1285-1288

[7] RING DERIVATIVES OF PHENOTHIAZINE - THE SYNTHESIS OF 1-SUBSTITUTED PHENO-THIAZINES BY THIONATION [J].

MASSIE, SP ;

KADABA, PK .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (03) :347-348

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