Journal
TETRAHEDRON LETTERS
Volume 85, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.153491
Keywords
Spirooxindole; Multicomponent reaction; Azomethine ylide; Cycloaddition reaction; 2,2,2-trifluoroethanol
Categories
Funding
- C.S.I.R. New Delhi
- DST (SERB) New Delhi [YSS/2015/000972]
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A series of new functionalized analogues of spirooxindole-pyrrolidines have been synthesized via 1,3-dipolar cycloaddition reaction strategy under efficient and eco-friendly conditions. The reaction formed a complex heterocyclic hybrid with multiple stereo centers in one step, showcasing a high regio- and exo-selective manner. Single crystal X-ray diffraction analysis was used to determine the regio-/stereochemistry.
A series of new functionalized analogues of spirooxindole-pyrrolidines have been synthesized by com-prising benzimidazo[2,1-b]thiazolidinone heterocyclic fused moiety via 1,3-dipolar cycloaddition reac-tion strategy under an efficient and eco-comfortable reaction conditions. In the present study a new dipolarophiles alkyl(Z)-2-(3-oxobenzo[4,5]imidazo[2,1-b]thiazol-2(3H)-ylidene)acetate reacts efficiently with non-stabilized 1,3-dipolar component azomethine ylide formed in situ from the reaction of substituted isatins and alpha-amino acid sarcosine to affording new complex heterocyclic hybrid i.e.,dispiro[benz-imidazo[2,1-b]thiazole-2,30-pyrrolidine-20,30'-indoline]-40-carboxylates. The present benzimidazo[2,1-b] thiazolidinone grafted dispirooxindole core system formed by the creation of two new C-C and one C-N bonds with multiple stereo centers in one-step operation and reaction proceed with highly regio and exo-selective manner. Further, the present approach is high yielding protocol for synthesis of target cycload-ducts in short reaction time using 2,2,2-trifluoroethanol (TFE) as an efficient reaction medium. The regio-/stereochemistry has been concluded by single crystal X-ray diffraction analysis. (C) 2021 Elsevier Ltd. All rights reserved.
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