Novel route for the synthesis of structurally diverse pyrrolo[2,1-a] isoquinoline in aqueous micellar medium

Tetrahedron Letters

Volumn 52, Issue 13, 2011, Pages 1527-1531

  Naskar, Subhendu ^a   Banerjee, Maitreyee ^a   Hazra, Abhijit ^a   Mondal, Shyamal ^a   Maity, Arindam ^a   Paira, Rupankar ^a   Sahu, Krishnendu B ^a   Saha, Pritam ^a   Banerjee, Sukdeb ^a   Mondal, Nirup B ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

1,3 Dipolar cycloaddition reaction; Chromone 3 carboxaldehyde; Micelle; Pyrrolo 2,1 a isoquinoline; Reactions in water

Indexed keywords

BROMINE DERIVATIVE; BROMOACETIC ACID; CHROMONE 3 CARBOXALDEHYDE; ISOQUINOLINE; PHENACYLBROMIDE; PYRROLO[2,1 A]ISOQUINOLINE; QUINOLINE DERIVATIVE; SURFACTANT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; REACTION TIME; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 79951949854     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.141     Document Type: Article

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35. General reaction procedure for the synthesis of pyrrolo[2,1-a] isoquinolines: One mmol each of the isoquinoline (1a-b), phenacyl bromide/bromoacetic acid ester (2a-j), and chromone-3-carboxaldehyde (3a-c) derivatives were taken in a 100 ml RB flask. Then water (50 ml), CTAB (4 mmol) and DBU (1 mmol) were added and the mixture was stirred continuously for 1 h at room temperature. After completion of the reaction (monitored by TLC), the contents of the reaction mixture were poured into a separating funnel and extracted with ethyl acetate (3 × 25 ml). The organic layer was washed thoroughly with water until free from CTAB and base, dried over sodium sulfate, and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was chromatographed over a column of silica gel (60-120 mesh) eluting with a mixture of hexane and ethyl acetate in different ratios, to yield the pyrrolo[2,1-a]isoquinolines (4a-x).
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