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1, 3-Dipolar cycloaddition reactions: Synthesis of 5-benzyl-1-(2′,4′-dibromophenyl)-3-(4″-substituted phenyl)-3a,4,6,6a-tetrahydro-1H, 5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives

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Abstract

1,3-Dipolar cycloaddition of nitrilimines 3 with N-benzyl maleimide 4 has provided 5-benzyl-1-(2′,4′-dibromophenyl)-3-(4″-substituted phenyl)-3a,4,6,6a-tetrahydro-1H,5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives 5 in excellent yield as the only isomer through a concerted pathway.

Nitrilimines have been prepared in situ by base catalysed dehydrohalogenation of hydrazonyl halides. Their cycloaddition with N-benzyl maleimides having carbon–carbon double bond has been carried out which leads to the synthesis of 5-benzyl-1-(2′,4′-dibromophenyl)-3-(4″-substituted phenyl)-3a,4,6,6atetrahydro-1H,5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives as the single isomer. Stereochemical studies revealed that addition follows cis-endo addition rule.

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Acknowledgements

The authors are thankful to the University Grant Commission (UGC), New Delhi, for financial assistance and the Sophisticated Analytical Instrumentation Facility (SAIF), Panjab University, Chandigarh and NIPER, Mohali for spectral analysis.

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  1. Department of Chemistry, Punjabi University, Patiala, 147 002, India

    MANPREET KAUR, BALDEV SINGH & BALJIT SINGH

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  1. MANPREET KAUR
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  2. BALDEV SINGH
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  3. BALJIT SINGH
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Correspondence to BALDEV SINGH.

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KAUR, M., SINGH, B. & SINGH, B. 1, 3-Dipolar cycloaddition reactions: Synthesis of 5-benzyl-1-(2′,4′-dibromophenyl)-3-(4″-substituted phenyl)-3a,4,6,6a-tetrahydro-1H, 5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives. J Chem Sci 125, 1529–1534 (2013). https://doi.org/10.1007/s12039-013-0526-3

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