FRIEDEL-CRAFTS CYCLIZATION OF 2-(3-INDOLYTHIO)PROPIONIC ACIDS - AN UNUSUAL REARRANGEMENT LEADING TO 4-SULFUR-SUBSTITUTED TRICYCLIC INDOLES

被引：4

作者：

CHUNG, JYL

REAMER, RA

REIDER, PJ

机构：

[1] Depament of Process Research Merek Research Laboratories Division of Merck, Co., Inc., Rahway

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 33期

关键词：

FRIEDEL-CRAFTS ACYLATION; REARRANGEMENT; TRICYCLIC-INDOLES; 4-THIO-INDOLES; THIOPYRANO-[4,3,2-C,D]INDOLES;

D O I：

10.1016/S0040-4039(00)61267-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular Friedel-Crafts acylation of 2-(3-indolythio)propionic acid 1 has been found to undergo an unprecedented rearrangement to provide a novel tricyclic indole having the sulfur substituted on C-4 rather than on the expected C-3. A mechanism for its formation is proposed. This rearrangement also proceeded with good optical retention when a chiral substrate was used.

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页码：4717 / 4720

页数：4

相关论文

共 19 条

[1] H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].

BAX, A ;

SUMMERS, MF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094

[2]

Chang C.-P., 1976, HUA HSUEH HSUEH PAO, V34, P133

[3] TRANSITION-METAL MEDIATED SYNTHESIS OF (+/-)-CHUANGXINMYCIN METHYL-ESTER [J].

DICKENS, MJ ;

MOWLEM, TJ ;

WIDDOWSON, DA ;

SLAWIN, AMZ ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (03) :323-325

[4] ARYLSULFENYLATION OF 2,3-DIALKYLINDOLES - PREPARATION OF 3-ARYLTHIOINDOLENINES AND THERMAL-CONVERSION TO AN N-SULFENYLINDOLE [J].

DMITRIENKO, GI ;

FRIESEN, RW ;

CARSON, L ;

VICE, SF .

TETRAHEDRON LETTERS, 1982, 23 (08) :821-824

[5]

FISCHER E, 1888, CHEM BER, V21, P1811

[6] ACID-CATALYZED ISOMERIZATION OF INDOL-3-YL SULFIDES TO INDOL-2-YL SULFIDES - UNEXPECTED INTERMOLECULAR NATURE OF THE REARRANGEMENT [J].

HAMEL, P ;

GIRARD, Y ;

ATKINSON, JG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (01) :63-65

[7]

HINO T, 1976, J CHEM SOC P1, V7, P745

[8] FORMATION OF A NOVEL THIOPYRANOINDOLE RING-SYSTEM [J].

HUTCHINSON, JH ;

MCEACHERN, EJ ;

SCHEIGETZ, J ;

MACDONALD, D ;

THERIEN, M .

TETRAHEDRON LETTERS, 1992, 33 (33) :4713-4716

[9] SYNTHETIC STUDIES IN THE INDOLE SERIES - PREPARATION OF THE UNIQUE ANTIBIOTIC ALKALOID CHUANGXINMYCIN BY A NITRO-GROUP DISPLACEMENT REACTION [J].

KOZIKOWSKI, AP ;

GRECO, MN ;

SPRINGER, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (26) :7622-7626

[10]

Liang H.-T., 1976, HUA HSUEH HSUEH PAO, V34, P129