A new synthesis of substituted 2(1H)‐pyrazinones

Abstract

The hydrohalides of 2‐sec‐aminoalkanenitriles on treatment with oxalyl halides in o‐dichlorobenzene at 80‐100° give 3, 5‐dihalo‐2(1H)‐pyrazinones, of which the 3‐halo substituent is easily replaced by nucleophiles. A reaction mechanism for the pyrazinone synthesis is proposed.

Development of a Functionalizable External β‐Turn Mimic Based on a cis‐Fused 1,7‐Naphthyridine Scaffold

“…[9] , starting from 4-methoxybenzylamine (26 13 C NMR (100 MHz, CDCl 3 ): δ ϭ 159.9 (C-4Ј), 151.5 (C-2), 147.0 (C-3), 130.3 (C-2 Ј , C-6Ј), 125.6, 125.1 (C-6, C-5), 123.8 (C-1Ј), 114.6 (C-3Ј, C-5Ј …”

Diastereoselective Diels–Alder Additions of Ethene to Substituted Homochiral 2(1H)‐Pyrazinones

“…The short and highly versatile synthesis of 3,5-dichloro-2(1H)-pyrazinones [1] is the starting point for many of the synthetic methods developed in our group.…”

Synthesis of N-Hydroxypyrazin-2(1H)-ones via Selective O-Debenzylation of 1-Benzyloxypyrazin-2(1H)-ones Using Flow Methodology

“…This explains their potential to inhibit specific metal-containing enzymes involved in human immunodeficiency virus [HIV] [2][3][4] and cancer progression (histone deacetylases [HDACs], mitochondrial membrane permeabilities [MMPs], ribonucleotide reductase [RNR]) [5][6][7]. Our group has previously been working on the design and synthesis of highly functionalized pyrazinones [8][9][10][11][12][13][14]. In the current paper, we focus on our newly developed synthesis of N-hydroxypyrazinones.…”