Expedient synthesis of N-fused indoles through an intramolecular [3+2]-cycloaddition approach

Synlett

Volumn , Issue 6, 2010, Pages 952-954

  Kathiravan, Subban ^a   Raghunathan, Raghavachary ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

Azomethine ylides; Baylis Hillman adducts; Indolo pyrrolo pyrroles; N fused indoles; Pyrrolo pyrrolizidines 1,3 dipolar cycloaddition

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77949877630     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219551     Document Type: Article

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38. Synthesis of N-Fused Indole 3a Typical Procedure A solution of 1a (1 mmol) and sarcosine 2 (1.5 mmol) in toluene (10 mL) was stirred and heated at reflux for 6 h. After evoperation of the solvent under reduced pressure, the crude product was purified by short column chromatography on silica gel (hexaneEtOAc, 5:95) to provide the product in 78% yield as viscous colorless oil. 1H NMR (300 MHz, CDCl3): d = 1.84 (s, 3 H), 2.36 (s, 3 H), 2.60 (s, 2 H), 3.25 3.38 (m, 1 H), 3.713.81 (m, 1 H), 3.74 (s, 3 H), 4.074.15 (m, 1 H), 4.81 (s, 1 H), 7.037.53 (m, 9 H). 13C NMR (75 MHz, CDCl3): d = 21.04, 39.66, 47.49, 49.65, 53.02, 59.33, 67.95, 104.52, 109.70, 118.91, 119.12, 121.26, 127.36, 128.51, 128.72, 132.08, 137.01, 138.46, 174.93. MS: m/z = 346.85 [M+]. Anal. Calcd for C22H24N2O2: C, 76.08; H, 6.62; N, 8.06. Found: C, 76.00; H, 6.57; N, 8.14.