N−H Insertion Reactions of Boc-Amino Acid Amides:  Solution- and Solid-Phase Synthesis of Pyrazinones and Pyrazines

Matsushita, Hana; Lee, Sang‐Hyeup; Yoshida, Kazuhiro; Clapham, Bruce; Koch, Guido; Zimmermann, J.; Janda, Kim D.

doi:10.1021/ol047933a

Cited by 54 publications

(25 citation statements)

References 16 publications

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“…488 Among other N−H functionalized insertion partners for diazocarbonyl substrates that have the potential to generate diverse heterocycles are ureas. Janda and co-workers have explored such reactions in solution and in the solid phase with a view to preparing libraries of small heterocycles for application in combinatorial-type screening programs for drug discovery.…”

Section: X−h Insertion Reactions Of Diazocarbonyl Compoundsmentioning

confidence: 99%

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Ford¹,

Miel

Ring³

et al. 2015

Chem. Rev.

1,328

585

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Section: X−h Insertion Reactions Of Diazocarbonyl Compoundsmentioning

confidence: 99%

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Ford¹,

Miel

Ring³

et al. 2015

Chem. Rev.

1,328

585

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“…1 H NMR (400 MHz), 13 C{ 1 H} NMR (100 MHz), and 19 F NMR (377 MHz) spectra were recorded on NMR spectrometer. Deuterated chloroform was used as the solvent and chemical shift values (δ) are reported in parts per million relative to the residual signals of this solvent [δ 7.26 for 1 H (chloroform-d), δ 2.05 for 1 H (acetone-d 6 ), δ 77.2 for 13 C{ 1 H} (chloroform-d), and δ 29.84, 206.26 for 13 C{ 1 H} (acetone-d 6 )]. Infrared spectra were recorded on FT-IR spectrometer as either a thin film pressed between two sodium chloride plates or as a solid suspended in a potassium bromide disk.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…12b,16c Ethyl 3-(4-Nitrophenyl)-2H-azirine-2-carboxylate (1a 4, 147.4, 138.8, 131.2, 129.8, 128.9, 128.8, 127.0, 126.7, 123.2, 118.8, 115.1, 56.0, 21.4;IR (film) 2916IR (film) , 1592IR (film) , 1268IR (film) , 1197IR (film) , 1166IR (film) , 1091IR (film) , 1006 2, 156.0, 142.7, 131.1, 130.0, 128.0, 127.4, 122.0, 121.0, 117.8, 115.0, 110.8, 56.0, 55.5;IR (film): 3076, 1592IR (film): 3076, , 1267IR (film): 3076, , 1022 4, 160.1, 147.2, 131.2, 130.2, 130.1, 126.9, 119.0, 118.4, 115.1, 111.1, 77.3, 56.0, 55.4;IR (film) 2943IR (film) , 1592IR (film) , 1269IR (film) , 1044IR (film) , 1024 146.0, 135.0, 131.3, 130.8, 130.3, 129.1, 126.8, 126.1, 124.1, 119.3, 115.2, 56.0;IR (film) 3143, 1292IR (film) 3143, , 1269IR (film) 3143, , 1022 5, 146.2, 134.9, 131.3, 129.3, 127.5, 127.3, 126.8, 118.9, 115.2, 56.0;IR (film) 3095, 1591IR (film) 3095, , 1267IR (film) 3095, , 1022 6, 145.9, 132.1, 131.4, 131.1, 130.7, 129.1, 126.8, 124.7, 123.2, 119.4, 115.3, 56.1;IR (film) 2944IR (film) , 1592IR (film) , 1269IR (film) , 1024 6, 146.9, 132.9, 132.0, 129.5, 128.6, 127.7, 123.2, 121.4, 116.3, 56.6;IR (film) 2976IR (film) , 1591IR (film) , 1267IR (film) , 1197IR (film) , 1019 6,145.8,131.4,130.9 (q,J = 32.5 Hz),126.2,126.02,…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of Pyrazines from Rhodium-Catalyzed Reaction of 2H-Azirines with N-Sulfonyl 1,2,3-Triazoles

2015

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“…This work has centered on the application of polymer-bound a-diazo-b-ketoesters as key building blocks for the DOS 46) of a series of heterocycle libraries, including oxazoles, 47) indoles, 48) imidazolones and imidazoles, 49,50) and pyrazinones and pyrazines (Scheme 10). 51) DOS is an emerging field involving the synthesis of combinatorial libraries of diverse small molecules for biological screening. 52) Rather than being directed toward a single biological target, DOS libraries can be used to identify new ligands for a variety of targets.…”

Section: Spos Aimed At Diversity-oriented Synthesis (Dos)mentioning

confidence: 99%

Solid-phase organic synthesis of heterocyclic compounds

Izumi

2006

J. Pestic. Sci.

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The establishment of an efficient method of synthesizing heterocycles is required for the development of pharmaceuticals and agrochemicals, since many bioactive compounds have a heterocyclic ring. It is also necessary to prepare libraries of small organic compounds for investigations of function and the discovery of more bioactive compounds in pharmaceutical and agrochemical chemistry. Combinatorial and parallel synthetic methodologies provide the main driving force for the preparation of libraries for applications in the discovery of lead compounds and high-throughput medicinal chemistry within the pharmaceutical industry. [1][2][3] Many different formats of high-throughput chemistry are available and solid-phase organic synthesis (SPOS) plays a pivotal role allowing the convenient handling of large numbers of synthetic intermediates. 4,5) Since the combinatorial chemistry first appeared in the early 1990s, the way drugs are discovered has changed dramatically. The SPOS strategy has been a strong tool for high throughput synthesis and combinatorial chemistry.6-9) Synthetic intermediates are retained on the support and can be, therefore, quickly separated from the reaction mixture without extraction, concentration, and purification. SPOS is thus particularly advantageous for multi-step iterative synthesis. Various solid-phase automated synthesizers have been developed and are now commercially available. Even though several synthesizers for solution synthesis have been developed, automation is essentially easier in solid-phase synthesis than solution synthesis. In particular, the automated synthesis of peptides and oligonucleotides has allowed their facile and rapid preparation and greatly contributed to the elucidation of their functions. However, SPOS is not without its drawbacks since often extended development times are required to optimize new solid-phase chemical reactions. Actually, many laboratories have been engaged in the development of novel solidphase linking strategies and chemical technologies. This paper describes recent findings in, and a useful method for, the synthesis of heterocycle and nitrogen heterocycle compounds. Selenium-based solid-phase chemistry to include nitrogen-containing heterocyclesNicolaou and co-workers have been engaged in the development of novel solid-phase linking strategies and chemical technologies aimed at the construction of discovery-oriented, natural product-like libraries. [10][11][12] Toward this end, several natural product-like templates have been tethered to a solidsupport utilizing an intramolecular, selenium-mediated cycloaddition procedure. Encouraged by their success in developing chemistry and technology to produce natural productlike libraries of oxygen-containing heterocycles and carbocyclic frameworks [13][14][15][16] and due to the potential utility of such libraries in chemical biology investigations, 17,18) they sought to expand the scope of this selenium-based solid-phase chemistry to include nitrogen-containing heterocycles. Recently, they reported t...

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N−H Insertion Reactions of Boc-Amino Acid Amides: Solution- and Solid-Phase Synthesis of Pyrazinones and Pyrazines

Cited by 54 publications

References 16 publications

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Modern Organic Synthesis with α-Diazocarbonyl Compounds

Synthesis of Pyrazines from Rhodium-Catalyzed Reaction of 2H-Azirines with N-Sulfonyl 1,2,3-Triazoles

Solid-phase organic synthesis of heterocyclic compounds

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