Molecular hybridization-guided one-pot multicomponent synthesis of chromanone-fused 3, 3′-pyrrolidinyl-dispirooxindoles through a 1, 3-dipolar cycloaddition reaction. Issue 9 (3rd May 2018)

• Record Type: Journal Article
• Authors: Gong, Yi; Wang, Guan-Lian; Wei, Qi-Di; Chen, Lin; Liu, Xiong-Li; Tian, Min-Yi; Yang, Jun; Feng, Ting-Ting; Zhou, Ying
• Is Part Of: Synthetic communications. Volume 48:Issue 9(2018)
• Page Start: 1016
• Page End: 1024
• Publication Date: 2018-05-03
• Subjects: 1, 3-Dipolar cycloaddition -- 1, 3-dipolarophiles -- 3, 3′-pyrrolidinyl-dispirooxindoles -- anticancer activities -- isatylidenyl-chromanones; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2018.1428753
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: A new methodology was developed for the synthesis of 3, 3′-pyrrolidinyl-dispirooxindoles3 through a 1, 3-dipolar cycloaddition event of isatylidenyl-chromanones2 with azomethine ylides (thermally generated in situ from isatins and sarcosine). The method gives an easy access to a series of highly functionalized products containing three consecutive stereocenters and vicinal spiroquaternary stereocenters fused in one ring structure with 15 examples in high yields (up to 82% yield) and good diastereoselectivity (up to >20:1), which makes possible the synthesis of libraries under similar circumstances. Moreover, the current method provides a convenient approach for the efficient incorporation of two biologically important scaffolds (chromanone and 3, 3′-pyrrolidinyl-dispirooxindoles). X-ray diffraction studies of one of the cycloadducts proved the structure and regiochemistry of the cycloaddition. In particular, their biological activity against human leukemia cells K562 and normal L929 cells has been evaluated. These results suggested that 3, 3′-pyrrolidinyl-dispirooxindoles3 may be potential leads for further biological screenings. GRAPHICAL ABSTRACT: