Brønsted Acid or Lewis Acid Catalyzed [3+3] Cycloaddition of Azomethine Imines with N-Benzyl Azomethine Ylide: A Facile Access to Bicyclic N-Heterocycles

Shuo-ning Li; Bin Yu; Jia Liu; Hong-lian Li; Risong Na

doi:10.1055/s-0035-1560506

Synlett, Table of Contents

Synlett 2016; 27(02): 282-286
DOI: 10.1055/s-0035-1560506

letter

Brønsted Acid or Lewis Acid Catalyzed [3+3] Cycloaddition of Azomethine Imines with N-Benzyl Azomethine Ylide: A Facile Access to Bicyclic N-Heterocycles

Authors

Shuo-ning Li

^aCollaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road NO.95, Zhengzhou 450002, P. R. of China
Bin Yu

^cSchool of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, P. R. of China
Jia Liu*

^aCollaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road NO.95, Zhengzhou 450002, P. R. of China

^bModern Experimental Technology Center (Management), Henan Agricultural University, Wenhua Road NO.95, Zhengzhou 450002, P. R. of China Email: risongna@163.com
Hong-lian Li

^aCollaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road NO.95, Zhengzhou 450002, P. R. of China
Risong Na*

^aCollaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Wenhua Road NO.95, Zhengzhou 450002, P. R. of China

^bModern Experimental Technology Center (Management), Henan Agricultural University, Wenhua Road NO.95, Zhengzhou 450002, P. R. of China Email: risongna@163.com

Abstract

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Abstract

1,3-Dipolar cycloaddition reactions are one of the most important methods to obtain diverse heterocycles with novel skeletons. We herein report the Brønsted acid or Lewis acid catalyzed [3+3] cycloaddition of azomethine imines with nonstabilized azomethine ylide generated in situ from an N-benzyl precursor, providing a clean and facile access to diverse bicyclic N-heterocycles in moderate to good yields for further biological testing. Also, the protocol developed achieved the formation of C–C and C–N bonds simultaneously in a single step.

Key words

cycloaddition - bicyclic N-heterocycles - azomethine imines - N-benzyl azomethine ylide - TFA - Zn(OTf)₂

Full Text

References

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8 General Procedure for the [3+3] Annulation Reaction of N-Benzyl-Substituted Compound 1 and Azomethine Imines 3 To a solution of azomethine imines 3 (0.02 mmol) and N-benzyl-substituted compound 1 (0.03 mmol, 1.5 equiv) at 0 °C in CH₂Cl₂ (2 mL) was added acid catalyst (0.002 mmol, 0.1 equiv), the reaction mixture was stirred in refrigerated precision water baths at 10 °C for 72 h (depending on TLC monitor), N-benzyl-substituted compound 1 (0.05 mmol, 2.5 equiv) was added during this period. After the completion of the reaction, the reaction mixture was cooled to 0 °C, and was diluted with sat. NaHCO₃ solution. The filtrate was concentrated under vacuum and purified by flash column (hexane–EtOAc, 1:9) to give the product 4.
9 Selected Spectral Data for Compound 4a Yield 71% for TFA-catalyzed reaction [70% yield for Zn(OTf)₂-catalyzed reaction]; white solid. ¹H NMR (400 MHz, CDCl₃): δ = 7.36–7.27 (m, 10 H), 4.91 (d, J = 11.3 Hz, 1 H), 3.78–3.68 (m, 4 H), 3.36–3.25 (m, 1 H), 2.96–2.89 (m, 1 H), 2.84–2.75 (m, 1 H), 2.69–2.60 (m, 2 H), 2.50–2.39 (m, 1 H). ¹³C NMR (101 MHz, CDCl₃): δ = 170.35, 138.03, 137.03, 129.04, 128.75, 128.52, 128.33, 127.74, 127.52, 66.99, 61.58, 58.68, 57.61, 47.96, 30.09. IR (film): ν_max = 3029, 2924, 2844, 1695, 1602, 1494, 1453, 1410, 1328, 1280, 1129, 1065, 1027, 929, 979, 758, 100, 633, 569, 529, 498, 466 cm^–1. HRMS (MALDI): m/z calcd for C₁₉H₂₂N₃O⁺ [M + H]⁺: 308.1757; found: 308.1763.

Supplementary Material

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