Synthesis of Spirohydantoins and Schiff Bases of Indenoquinoxalinones and Indenopyridopyrazinones

J.H. Song1,*,, S.M. Bae1,, H.Y. Shin1,, D.I. Jung1, and J.H. Cho2,*

1Department of Chemistry, Dong-A University, Busan 604-714, Republic of Korea

2Department of Medical Biotechnology, Dong-A University, Busan 604-714, Republic of Korea

*Corresponding authors: E-mail: jhsong@dau.ac.kr, jhcho@dau.ac.kr

Abstract

The main structure of many compounds containing spirohydantoin and Schiff bases of indenoquinoxalines and indenopyridopyrazinones expose valuable pharmacological properties. Herein, an effective synthesis and stereochemistry of indenoquinoxalinones (2a, 2b+bi~2d+di) and indenopyridopyrazinones (2e+ei~g+gi) via the reaction of ninhydrin with desirable diamines is reported. We synthesized the corresponding spirohydantoins (3a, 3b~d and 3bi~di) from synthesized indeno[1,2-b]quinoxalinones and indeno[1,2-b]pyrido[3,2-e]pyrazinones with the standard Bucherer-Bergs conditions (KCN, ammonium carbonate, acetonitrile, refluxing, without NaHSO3). And also synthesized the azomethine analogs (4~8+8i) of tetracyclic indeno[1,2-b]quinoxalinones as a Schiff base.

Keywords

Spirohydantoin, Indenoquinoxalinones, Indenopyridopyrazinones, Ninhydrin, Diamine.

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