The Preparation of Hydroxypyrazines and Derived Chloropyrazines

Karmas, George; Spoerri, Paul E.

doi:10.1021/ja01126a070

Cited by 102 publications

(62 citation statements)

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“…Starting materials were purchased from Aldrich, Lancaster, Acros, and Merck. The known compounds 3c, [26] 3f, [27] 3g, [28] and 3m [29] were prepared according to literature. TLC analysis was performed on Merck silica gel 60F254 plate or Merck Al 2 O 3 60F 254 neutral (Typ E) plates and visualized with UV illumination.…”

Section: Methodsmentioning

confidence: 99%

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New calcineurin inhibiting 3-dimethylaminopropyl substituted diarylheterocycles by sonogashira reactions and catalytic hydrogenation

Yin

Liebscher

Erdmann

2005

Journal of Heterocyclic Chemistry

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A series of calcineurin inhibiting compounds 1 consisting of a central aromatic N‐heterocycle, two aryl substituents and a 3‐dimethylaminopropyl chain was synthesized by introduction of the side chain. A corresponding haloheterocycle 3 was transformed into a 3‐dimethylaminopropynylheterocycle 2 by Sonogashira coupling and was in turn hydrogenated in the presence of Pd/C to afford the 3‐dimethylaminopropyl‐sub‐stiuted heterocycles 1. Some of the products showed calcineurin inhibiting activity.

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Section: Methodsmentioning

confidence: 99%

“…Compounds 3c, [26] 3f, [27] 3g, [28] and 3m, [29] were known and prepared by corresponding literature. The haloheterocycles 3h, 3i and 3l were obtained by halogenation of halogen free analogues of 4 with NIS or NBS, respectively, while the 4-iodopyrimidine 3b was synthesized from the corresponding chloropyrimidine 5 and hydroiodic acid (Scheme 2).…”

mentioning

confidence: 99%

New calcineurin inhibiting 3-dimethylaminopropyl substituted diarylheterocycles by sonogashira reactions and catalytic hydrogenation

Yin

Liebscher

Erdmann

2005

Journal of Heterocyclic Chemistry

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“…3,5-Dimethylpyrazin-2-one was synthesized from pyruvaldehyde and L-alaninamide as described in Helliwell et al (2006) that was an adaption of the method of Karmas and Spoerri (1952);m.p. 148-150°C;lit.…”

Section: Synthesis Of Chemical Standardsmentioning

confidence: 99%

Sugar-Driven Prebiotic Synthesis of 3,5(6)-Dimethylpyrazin-2-one: A Possible Nucleobase of a Primitive Replication Process

Weber

2008

Orig Life Evol Biosph

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Reaction of glyceraldehyde with alanine amide (or ammonia) under anaerobic aqueous conditions yielded 3,5(6)-dimethylpyrazin-2-one that is considered a possible complementary residue of a primitive replicating molecule that preceded RNA. Synthesis of the dimethylpyrazin-2-one isomers under mild aqueous conditions (65 degrees C, pH 5.5) from 100 mM glyceraldehyde and alanine amide (or ammonia) was complete in about 5 days. This synthesis using 25 mM glyceraldehyde and alanine amide gave a total pyrazinone yield of 9.3% consisting of 42% of the 3,5-dimethylprazin-2-one isomer and 58% of the 3,6-dimethylpyrazin-2-one isomer. The related synthesis of the dimethylpyrazin-2-one isomers from glyceraldehyde and ammonia was about 200-fold less efficient than the alanine amide reaction. This synthetic process is considered a reasonable model of origin-of-life chemistry because it uses plausible prebiotic substrates, and resembles modern biosynthesis by employing the energized carbon groups of sugars to drive the synthesis of small organic molecules. Possible sugar-driven pathways for the prebiotic synthesis of polymerizable 2-pyrazinone monomers are discussed.

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“…Here, we chose haloheterocycles 3a -3m as starting materials (Figure 1). Compounds 3c, [26] 3f, [27] 3g, [28] and 3m, [29] were known and prepared by corresponding literature. The haloheterocycles 3h, 3i and 3l were obtained by halogenation of halogen free analogues of 4 with NIS or NBS, respectively, while the 4-iodopyrimidine 3b was synthesized from the corresponding chloropyrimidine 5 and hydroiodic acid (Scheme 2).…”

mentioning

confidence: 99%

New Calcineurin Inhibiting 3‐Dimethylaminopropyl Substituted Diarylheterocycles by Sonogashira Reactions and Catalytic Hydrogenation

2006

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The Preparation of Hydroxypyrazines and Derived Chloropyrazines

Cited by 102 publications

References 0 publications

New calcineurin inhibiting 3-dimethylaminopropyl substituted diarylheterocycles by sonogashira reactions and catalytic hydrogenation

New calcineurin inhibiting 3-dimethylaminopropyl substituted diarylheterocycles by sonogashira reactions and catalytic hydrogenation

Sugar-Driven Prebiotic Synthesis of 3,5(6)-Dimethylpyrazin-2-one: A Possible Nucleobase of a Primitive Replication Process

New Calcineurin Inhibiting 3‐Dimethylaminopropyl Substituted Diarylheterocycles by Sonogashira Reactions and Catalytic Hydrogenation

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