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June 20, 2026European Journal of Organic Chemistry0 citations

Asymmetric Synthesis of Spiro indoline‐3,1′‐pyrazolo[1,2‐ a pyridazine] Derivatives via Organocatalytic One‐Pot Domino Reaction

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LSLuying SongHCHongming CuiYLYuqing Lei

Key Points

  • This research aims to develop an efficient method for synthesizing spiro indoline-pyrazolo-pyridazine derivatives using an organocatalyst.
  • Organocatalytic domino reaction combining Knoevenagel, Michael, and cyclization mechanisms.
  • Reactions carried out with isatins, active methylene compounds, and maleic hydrazide.
  • Optimized conditions achieved significant enantiomer excess up to 98%.
  • Middle yields of spiro compounds ranging from 55% to 70%.
  • Enantiomer excess (ee) achieved up to 98%.
  • Validates the use of quinine-derived squaramide as an effective organocatalyst.

Abstract

Asymmetric synthesis of spiro indoline‐3,1′‐pyrazolo[1,2‐ a pyridazine] derivatives was first developed through an organocatalysed domino Knoevenagel/Michael/cyclization reaction using a quinine‐derived squaramide. Under the optimized conditions, the three‐component reaction of isatins, the active methylene compounds and maleic hydrazide yields the new type of spiro‐heterocycle compounds in middle yields (55%–70%) with up to 98% enantiomer excess (ee).

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Cite This Study

Song et al. (2026) studied this question.

synapsesocial.com/papers/6a362f3bdb0793dc1a536b04https://doi.org/10.1002/ejoc.70631
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