Tetrahedron

Synthesis of 3, 7-dihydroimidazo [1, 2a] pyrazine-3-ones and their chemiluminescent properties

M Adamczyk, SR Akireddy, DD Johnson, PG Mattingly…

Index: Adamczyk, Maciej; Akireddy, Srinivasa Rao; Johnson, Donald D.; Mattingly, Phillip G.; Pan, You; Reddy, Rajarathnam E. Tetrahedron, 2003 , vol. 59, # 41 p. 8129 - 8142

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Citation Number: 46

Abstract

A series of 3, 7-dihydroimidazo [1, 2a] pyrazine-3-ones were prepared from 2-amino-3, 5- dibromopyrazine. The concise synthesis of coelenterazine (5j), in three steps, 48% overall yield and> 99% purity exemplifies the strategy. Further, the synthetic approach facilitated the regiospecific incorporation of carboxyalkyl linkers on the 3, 7-dihydroimidazo [1, 2a] pyrazine-3-one nucleus that are required for bioconjugation. Peroxymonocarbonate, an ...

~12%

~62%

~58%

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