On Reuben G. Jones synthesis of 2-hydroxypyrazines

• Pierre Legrand and
• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 935–943, doi:10.3762/bjoc.18.93

• , this has never been the subject of a report. Our recent interest in the preparation of 3,5-substituted-2-hydroxypyrazines (3, R2 = Ar and R3 = CH2Ar) as intermediates for the synthesis of marine luciferins analogues [29][30] along with the simplicity of this access drove us to study some of its aspects

Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate

• Eloi P. Coutant,
• Vincent Hervin,
• Glwadys Gagnot,
• Candice Ford,
• Racha Baatallah and
• Yves L. Janin

Beilstein J. Org. Chem. 2018, 14, 2853–2860, doi:10.3762/bjoc.14.264

• -bromo-α-hydroxyiminocarboxylate and various alkylfuranes. Keywords: α-amino ester; α-hydroxyimino ester; [2 + 4] cycloadditions; [2 + 3] cycloadditions; Knoevenagel; nitrosoacrylate; Suzuki–Miyaura; Introduction Our current work on the chemistry of imidazo[1,2-a]pyrazin-3(7H)-one luciferins [1] has

Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions

• Glwadys Gagnot,
• Vincent Hervin,
• Eloi P. Coutant,
• Sarah Desmons,
• Racha Baatallah,
• Victor Monnot and
• Yves L. Janin

Beilstein J. Org. Chem. 2018, 14, 2846–2852, doi:10.3762/bjoc.14.263

• -amino esters was achieved using gold(I) chemistry. Keywords: α-amino ester; α-nitro esters; cerium ammonium nitrate; cycloaddition; gold(I) cyclization; Introduction In the course of our work on an original synthesis of imidazo[1,2-a]pyrazin-3(7H)-one luciferins [1], a large variety of racemic α-amino

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

• Jacob R. Hauser,
• Hester A. Beard,
• Mary E. Bayana,
• Katherine E. Jolley,
• Stuart L. Warriner and
• Robin S. Bon

Beilstein J. Org. Chem. 2016, 12, 2019–2025, doi:10.3762/bjoc.12.189

• -cyanobenzothiazoles; DABCO; luciferins; organocatalysis; Introduction Functionalised 2-cyanobenzothiazoles (CBTs, 1) are key building blocks for the synthesis of luciferins 3 [1][2][3], substrates of natural and engineered firefly luciferases that are widely used for bioluminescence imaging (BLI) [4][5]. The typical

• preparation of luciferins 3 involves straightforward condensation of CBTs 1 with D-cysteine (2) (Scheme 1). For BLI applications, luciferins are often generated in vivo from CBTs [4][5][6][7], which are easier to modify and handle due to their higher stability, cell permeability, and reactivity than the full

• power; QDose: power generated due to the temperature and heat capacity of the feed; energy: heat energy. Because QDose ≈ 0 over the course of the experiment, traces for QComp (orange) and QTotal (blue) overlap. Functionalised CBTs 1 can be used for the synthesis of luciferins 3 and for bioorthogonal