DIELS-ALDER CYCLOADDITION REACTIONS OF ENAMINOTHIONES WITH NITROALKENES

被引：23

作者：

BARUAH, PD ^{[1
]}

MUKHERJEE, S ^{[1
]}

MAHAJAN, MP ^{[1
]}

机构：

[1] NE HILL UNIV,DEPT CHEM,SHILLONG 793003,MEGHALAYA,INDIA

来源：

TETRAHEDRON | 1990年 / 46卷 / 06期

关键词：

D O I：

10.1016/S0040-4020(01)89763-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder cycloaddition reactions of enaminothiones (1) with nitroalkenes (2) result in very good yields (78-90%) of (2R,3S,4R)-6-aryl-2-aryl/furyl-3,4-dihydro-4-dimethylamino-3-nitro-2H-thiopyrans (3) as exclusive stereoisomers. The reactions of 3-N-arylamino-1-phenylpropene-1-thiones (5) with 2leading to stereospecific formation of (2R,3S,4S)-2-aryl-4-arylamino-3-nitro-6-phenyl-3,4-dihydro-2H-thiopyrans (6) and their conversions to thermodynamically more stable (2R,3S,4R)-2-aryl-4-arylamino-3-nitro-6-phenyl-3, 4-dihydro-2H-thiopyrans (7) is also reported. © 1990.

引用

页码：1951 / 1962

页数：12

共 22 条

[1] STEREOCHEMISTRY AND STRUCTURE IN TETRAHYDRO-1-THIO-4-PYRONE AND TETRAHYDRO-4-PYRONE SERIES [J].

BAXTER, CAR ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (09) :1174-&

[2]

BIGNEBAT J, 1969, B SOC CHIM FR, P127

[3]

BOGER DL, 1987, HETERO DIELSALDER ME, P214

[4] BICYCLIC 1,2-OXAZINE N-OXIDES - DIFFERENT BEHAVIOR IN RING FISSION BETWEEN SYSTEMS DERIVED FROM 5-MEMBERED AND 6-MEMBERED RING CYCLIC ENAMINES [J].

DANEO, S ;

PITACCO, G ;

RISALITI, A ;

VALENTIN, E .

TETRAHEDRON, 1982, 38 (10) :1499-1503

[5] INTERMOLECULAR [4 + 2]-CYCLOADDITIONS OF NITROALKENES WITH CYCLIC OLEFINS - TRANSFORMATIONS OF CYCLIC NITRONATES [J].

DENMARK, SE ;

CRAMER, CJ ;

STERNBERG, JA .

HELVETICA CHIMICA ACTA, 1986, 69 (08) :1971-1989

[6] CONFORMATIONS .6. VINYL-ALLYLIC PROTON SPIN COUPLINGS [J].

GARBISCH, EW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5561-+

[7]

GUEMAS JP, 1984, SULFUR LETT, V2, P121

[8] ORBITAL SYMMETRIES AND ENDO-EXO RELATIONSHIPS IN CONCERTED CYCLOADDITION REACTIONS [J].

HOFFMANN, R ;

WOODWARD, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (19) :4388-&

[9] DITHIOLE SERIES .2. REACTIONS OF 1,2- AND 1,3-DITHIOLIUM SALTS WITH NUCLEOPHILIC REAGENTS [J].

LEAVER, D ;

MCKINNON, DM ;

ROBERTSO.WA .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JAN) :32-&

[10] NEW SYNTHESIS OF ISOXAZOLES AND ISOTHIAZOLES - A CONVENIENT SYNTHESIS OF THIOENAMINONES FROM ENAMINONES [J].

LIN, YI ;

LANG, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (24) :4857-4860

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