Synthesis of 2,3-Dihydrotryptamines from Amide Solvents and Acyclic Materials through Metal-Free Amidoalkylarylation of Unactivated Alkenes

Yubin Ji; Siping Yang; Shiyi Lin; Yan Wang; Chenfeng Ji; Yingjie Liu; Deqiang Liang

doi:10.1055/s-0037-1611825

Synlett, Table of Contents

Synlett 2019; 30(11): 1329-1333
DOI: 10.1055/s-0037-1611825

letter

Synthesis of 2,3-Dihydrotryptamines from Amide Solvents and Acyclic Materials through Metal-Free Amidoalkylarylation of Unactivated Alkenes

Yubin Ji

^aResearch Center on Life Sciences and Environmental Sciences, Harbin University of Commerce, Harbin 150076, P. R. of China Email: liuyj691@nenu.edu.cn

,

Siping Yang

^bYunnan Engineering Technology Research Center for Plastic Films, Department of Chemistry, Kunming University, Kunming 650214, P. R. of China Email: liangdq695@nenu.edu.cn

,

Shiyi Lin

^bYunnan Engineering Technology Research Center for Plastic Films, Department of Chemistry, Kunming University, Kunming 650214, P. R. of China Email: liangdq695@nenu.edu.cn

,

Yan Wang

^bYunnan Engineering Technology Research Center for Plastic Films, Department of Chemistry, Kunming University, Kunming 650214, P. R. of China Email: liangdq695@nenu.edu.cn

,

Chenfeng Ji

^aResearch Center on Life Sciences and Environmental Sciences, Harbin University of Commerce, Harbin 150076, P. R. of China Email: liuyj691@nenu.edu.cn

,

Yingjie Liu*

^aResearch Center on Life Sciences and Environmental Sciences, Harbin University of Commerce, Harbin 150076, P. R. of China Email: liuyj691@nenu.edu.cn

,

Deqiang Liang *

^bYunnan Engineering Technology Research Center for Plastic Films, Department of Chemistry, Kunming University, Kunming 650214, P. R. of China Email: liangdq695@nenu.edu.cn

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Abstract

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Abstract

The first synthesis of 2,3-dihydrotryptamines from acyclic materials and an exo-selective amidoalkylation/cyclization cascade of N-allyl anilines through α-C(sp³)–H functionalization of simple amides across unactivated alkenes are presented. This reaction proceeds in mixed aqueous media and under metal-free conditions and features a broad substrate scope and a simple operation.

Key words

amides - cross-coupling - cyclization - green chemistry - radical reaction - tandem reaction

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References

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21 General Procedure for the Synthesis of 2,3-Dihydrotryptamines (2a1 as an Example) A 10 mL Schlenk tube, equipped with a magnetic stirring bar, was charged under argon with N-(2-methylallyl)-N-phenylacetamide (1a1, 38 mg, 0.2 mmol), DCP (162 mg, 0.6 mmol), DMA (1.0 mL), and H₂O (0.2 mL). The mixture was stirred at 120 °C for 6 h, then it was quenched with saturated aqueous Na₂S₂O₃ (0.5 mL) and water (5.0 mL) and extracted with CH₂Cl₂ (10.0 mL) three times. The residue obtained after evaporation of the solvent was purified by flash column chromatography on silica gel (petroleum ether/acetone = 6:1, v/v) to afford N-[2-(1-acetyl-3-methylindolin-3-yl)ethyl]-N-methylacetamide (2a1) as a pale-yellow oil (39 mg, 71% yield) as a 20:10:3:2 inseparable mixture of 4 rotamers (major, minor, and two more isomers appearing in minute quantities, and only the major and the minor are characterized) due to the restricted rotation of the N–(CO) bonds. ¹H NMR (400 MHz, CDCl₃): δ = 1.38 (s, 3 H major), 1.43 (s, 3 H minor), 1.79–1.98 (stack, 2 H major and 5 H minor), 2.02 (s, 3 H major), 2.24 (s, 3 H minor), 2.25 (s, 3 H major), 2.84 (s, 3 H minor), 2.87 (s, 3 H major), 2.95–3.04 (stack, 1 H major and 1 H minor), 3.16–3.24 (m, 1 H minor), 3.42–3.49 (m, 1 H major), 3.72 (d, J = 10.4 Hz, 1 H major), 3.78 (d, J = 10.3 Hz, 1 H minor), 3.87 (d, J = 10.4 Hz, 1 H minor), 4.11 (d, J = 10.4 Hz, 1 H major), 7.03–7.13 (stack, 2 H major and 2 H minor), 7.19–7.27 (stack, 1 H major and 1 H minor), 8.19 (d, J = 8.1 Hz, 1 H major), 8.22 (d, J = 8.1 Hz, 1 H minor). ¹³C{¹H} NMR (100 MHz, CDCl₃): δ = 170.3 (major), 170.0 (minor), 168.8 (major), 168.5 (minor), 142.12 (minor), 142.08 (major), 138.2 (major), 137.0 (minor), 128.5 (minor), 128.0 (major), 124.1 (minor), 123.8 (major), 122.1 (major), 122.0 (minor), 117.2 (minor), 117.0 (major), 61.1 (minor), 60.8 (major), 46.8 (minor), 44.1 (major), 42.5 (major), 42.3 (minor), 39.8 (minor), 38.3 (major), 36.2 (major), 33.3 (minor), 27.2 (major and minor), 24.32 (major), 24.29 (minor), 21.8 (major), 20.9 (minor). HRMS (ESI-TOF): m/z calcd for C₁₆H₂₃N₂O₂ ⁺ [M + H]⁺: 275.1754; found: 275.1762.

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