Divergent synthesis of pyrrolidone fused pyrimido[1,2- b]indazole through selective trapping of an enone intermediate by 1 H-indazol-3-amine

Xi Shen; Zhi-Cheng Yu; You Zhou; Yan-Dong Wu; An-Xin Wu

doi:10.1039/d4cc03483j

Divergent synthesis of pyrrolidone fused pyrimido[1,2- b]indazole through selective trapping of an enone intermediate by 1 H-indazol-3-amine

Chem Commun (Camb). 2024 Sep 5;60(72):9781-9784. doi: 10.1039/d4cc03483j.

Authors

Xi Shen¹, Zhi-Cheng Yu¹, You Zhou¹, Yan-Dong Wu¹, An-Xin Wu^{1

2}

Affiliations

¹ National Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.
² State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China. chwuax@mail.ccnu.edu.cn.

PMID: 39158556
DOI: 10.1039/d4cc03483j

Abstract

An oxidant-controlled divergent synthesis of a pyrrolidone fused pyrimido[1,2-b]indazole skeleton was developed through selective cyclization of an in situ generated enone intermediate and 1H-indazol-3-amine. The one-pot, metal-free process formed three C-N bonds, one C-C bond, and a tetrasubstituted carbon stereocenter containing a hydroxyl group. This method not only allowed for the synthesis of over 60 new pyrrolidone fused pyrimido[1,2-b]indazole derivatives, but was also compatible with the transformation of complex active molecules and the derivation of target products. Significantly, product 4q exhibited aggregation-induced emission (AIE) characteristics without any further modification.