A NEW ROUTE TO HETEROCYCLIC FUSED 2,5-DIHYDROTHIOPHENE S,S-DIOXIDES - FORMATION OF PYRAZOLE ANALOGS OF ORTHO-XYLYLENES

被引：19

作者：

CHALONER, LM

CREW, APA

STORR, RC

YELLAND, M

机构：

[1] UNIV LIVERPOOL,SCH CHEM,POB 147,LIVERPOOL L69 3BX,ENGLAND

[2] ICI FINE CHEM MFG ORG,MANCHESTER M9 3DA,ENGLAND

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 51期

关键词：

2,5-DIHYDROTHIOPHENE S,S-DIOXIDES; DIAZOMETHANE ADDITION; HETEROCYCLIC XYLYLENES; DIHYDRO-BIS-METHYLENEPYRAZOLES;

D O I：

10.1016/0040-4039(91)80547-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of diazomethane to 3-phenylsulphonyl-2,5-dihydrothiophene S,S-dioxide 3, followed by base induced aromatisation gives the sulphone 7, a precursor to pyrazole analogues of omicron-xylylene (omicron-quinodimethane).

引用

页码：7609 / 7612

页数：4

共 9 条

[1] CONDENSED CYCLOBUTANE AROMATIC COMPOUNDS .6. THE PYROLYSIS OF 1,3-DIHYDROISOTHIANAPHTHENE-2,2-DIOXIDE - A NEW SYNTHESIS OF BENZOCYCLOBUTENE [J].

CAVA, MP ;

DEANA, AA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (16) :4266-4268

[2] HETEROCYCLIC O-XYLYLENES - THIAZOLE, OXAZOLE AND IMIDAZOLE ANALOGS [J].

CHAUHAN, PMS ;

CREW, APA ;

JENKINS, G ;

STORR, RC ;

WALKER, SM ;

YELLAND, M .

TETRAHEDRON LETTERS, 1990, 31 (10) :1487-1490

[3] A FACILE SYNTHESIS OF STABLE PRECURSORS TO 2-ALKYLATED AND 2,3-DIALKYLATED 1,3-BUTADIENES [J].

CHOU, SSP ;

SUN, CM .

TETRAHEDRON LETTERS, 1990, 31 (07) :1035-1038

[4] FACILE SYNTHESIS OF 4,6-DIHYDROTHIENO[3,4-B]THIOPHENE 5,5-DIOXIDE - A SYNTHETIC EQUIVALENT OF 2,3-DIHYDRO-2,3-DIMETHYLENETHIOPHENE [J].

CHOU, TS ;

TSAI, CY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) :1287-1288

[5] THE GENERATION OF 2,3-DIHYDRO-2,3-BIS-(METHYLENE)THIOPHENES FROM 4,6-DIHYDROTHIENO[3,4-B]THIOPHENE 5,5-DIOXIDES [J].

CREW, APA ;

JENKINS, G ;

STORR, RC ;

YELLAND, M .

TETRAHEDRON LETTERS, 1990, 31 (10) :1491-1494

[6]

Houk K. N., 1984, 1 3 DIPOLAR CYCLOADD, V2, P407

[7] THE PYRAZOLE ANALOG OF ORTHO-QUINODIMETHANE - GENERATION AND CYCLOADDITION REACTIONS [J].

MITKIDOU, S ;

STEPHANIDOUSTEPHANATOU, J .

TETRAHEDRON LETTERS, 1990, 31 (36) :5197-5200

[8] REACTIONS OF DIAZO COMPOUNDS .8. REACTION OF DIAZOMETHANE WITH ALPHA,BETA-UNSATURATED SULFONES [J].

PARHAM, WE ;

BLAKE, FD ;

THEISSEN, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (07) :2415-&

[9] 3,4-DIMETHYLENEFURAN AND 3,4-DIMETHYLENETHIOPHENE, HETEROCYCLIC-ANALOGS OF THE DISJOINT NON-KEKULE HYDROCARBON TETRAMETHYLENEETHANE [J].

STONE, KJ ;

GREENBERG, MM ;

GOODMAN, JL ;

PETERS, KS ;

BERSON, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8088-8089

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