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Volumn 29, Issue 15, 1988, Pages 1799-1802

Palladium catalyzed reaction of 2-alkynylanilines with allyl chlorides. Formation of 3-allylindoles

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[No Author keywords available]

Indexed keywords

EID: 0001628407 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)82047-X Document Type: Article

Times cited : (204)

References (19)

1
- 0004125888
- Springer-Verlag, Berlin
- (1980) Organic Synthesis with Palladium Compound
- Tsuji¹

2
- 0003624033
- Academic Press, London
- (1985) Palladium Reagents in Organic Syntheses
- Heck¹

6
- 0002913891
- (1987) Heterocycles , vol.25 , pp. 297
- Fukuda¹ Utimoto² Nozaki³

7
- 0001216247
- (1984) Tetrahedron Lett. , vol.25 , pp. 5323
- Lambert¹ Utimoto² Nozaki³

8
- 0000955337
- (1981) Tetrahedron Lett. , vol.22 , pp. 4277
- Utimoto¹ Miwa² Nozaki³

10
- 84918471418
- Copper catalyzed intramolecular cyclization of 2-alkynylanilines to give indoles was reported (ref. 11, 12).

11
- 0002082317
- (1966) J. Org. Chem. , vol.31 , pp. 4071
- Castro¹ Gaughan² Owsley³

12
- 0000762979
- and references cited therein.
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 7177
- Fujiwara¹ Fukutani² Sano³ Mauroka⁴ Yamamoto⁵

13
- 37049088366
- Ruthenium catalysed N-heterocyclisation: indoles from 2-aminophenethyl alcohols
- Indoles from aniline derivatives under Ru catalysis
- (1986) Journal of the Chemical Society, Chemical Communications , pp. 1575
- Tsuji¹ Huh² Yokoyama³ Watanabe⁴

14
- 0000688298
- (1986) J. Org. Chem. , vol.51 , pp. 5499
- Iritani¹ Yanagihara² Utimoto³

16
- 84989498349
- A Convenient Synthesis of Ethynylarenes and Diethynylarenes
- (1980) Synthesis , pp. 627
- Takahashi¹ Kuroyama² Sonogashira³ Hagihara⁴

17
- 84918471417
- 4, and concentrated. Chromatography (silica gel/hexane-ethyl acetate) of the crude product gave 140 mg (81% yield) of 2-butylindole.

18
- 84918471416
- 2 (13 mg, 0.05 mmol) are added under argon atmosphere, and the whole was stirred overnight at room temperature. Aqueous workup, extraction with ether, concentration, and chromatographic purification (silica gel) of the reaction mixture gave N-carbomethoxy-3-allyl-2-butylindole (210 mg, 73% yield) and N-carbomethoxy-2-butylindole (5% yield). Analogous results are obtained by the use of 2,2-dimethyloxirane, in place of methyloxirane.

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