Microwave-induced solid-supported Fischer indolization, a key step in the total synthesis of the sempervirine type methoxy analogues

Tetrahedron Letters

Volumn 45, Issue 48, 2004, Pages 8831-8834

  Lipińska, Teodozja ^a  

^a SIEDLCE UNIVERSITY OF NATURAL SCIENCES AND HUMANITIES   (Poland)

Author keywords

2 Heteroaryl 5 methoxyindoles; Fischer indole synthesis; Microwaves; Sempervirine type methoxy analogues; Solid support

Indexed keywords

INDOLE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLIZINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; MICROWAVE RADIATION; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 7444221713     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.008     Document Type: Article

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19. 2) was added. After mixing manually, the solvent was evaporated under reduced pressure. The resulting supported substrate was placed into four identical Pyrex vials, which were fitted in turn into a Pyrex cylindrical vessel and irradiated in a Synthewave 402 microwave reactor (Prolabo, 300 W, open system). The temperature setpoint was programmed at 140°C or 150°C (Fig. 1: temp adjusted). Irradiation was stopped after 2-2.5 min from the moment the temperature began rapidly increasing. The solids from the vials were cooled and extracted several times with diethyl ether (100 mL) and diethylamine (2 mL). The residue obtained after evaporation of the solvent was purified by column chromatography on silica gel (Merck, 100-200 mesh) to afford the pure products: 7b (eluted with chloroform) or 4a-d (eluted with chloroform-hexane 2:1). The yields and physical properties of products 7b and 4a-d are shown in Table 1
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