By Desmond J. Brown, Edward C. Taylor, Jonathan A. Ellman
This quantity within the Chemistry of Heterocyclic Compounds sequence offers a finished evaluate of the quinoxaline literature from 1975 to the current (2002), updating Volumes five and 35 . It presents an alphabetical desk of identified easy quinoxalines, together with new compounds mentioned during this quantity and their actual information, in addition to the pyrazines from the unique volumes. organic actions, spectral or different actual reports, and different such fabrics look at applicable issues within the textual content. The in-depth assurance contains synthesis, reactions, spectroscopic, and actual homes for every category of compounds.
Chemistry of Heterocyclic Compounds, quantity sixty one: complement II presents the main up to date summation of information of the artificial chemistry of quinoxalines.
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This quantity within the Chemistry of Heterocyclic Compounds sequence provides a complete evaluation of the quinoxaline literature from 1975 to the current (2002), updating Volumes five and 35 . It presents an alphabetical desk of recognized uncomplicated quinoxalines, together with new compounds mentioned during this quantity and their actual facts, in addition to the pyrazines from the unique volumes.
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Extra resources for The Chemistry of Heterocyclic Compounds, Quinoxalines: Supplement II
HC(À ÀCÀ ÀO)À À ÀN] grouping. For convenience, discussion of this synthesis is subdivided according to the type of synthon used to produce formally aromatic quinoxalines; the formation of similar ring-reduced quinoxalines (mostly from related synthons at a lower oxidation state) is included in each such category. 1. Using a Dialdehyde (Glyoxal) or Related Synthon Commercial 40% aqueous glyoxal or the glyoxal–sodium bisulfite adduct may be used satisfactorily with o-phenylenediamines to afford 2,3-unsubstituted quinoxalines; the use of an irregular synthon or substrate is also illustrated in the following examples.
14. Using a Diacyl Dihalide (Oxalyl Halide) or Related Synthon Like the preceding category, this is poorly represented in recent literature, although it has significant potential, as illustrated in the following examples. 4. When the Synthon Supplies N1 þ C2 þ C3 of the Quinoxaline This type of cyclocondensation has not been developed to any extent. However, the following examples indicate that it could eventually become a valuable procedure. 5. (308) (309) When the Synthon Supplies N1 þ C2 þ C3 þ N4 of the Quinoxaline Although intrinsically unappealing, this category of synthesis has been used occasionally in several forms, especially with cyclohexane rather than benzene substrates.
Keto esters and the like have 32 Primary Syntheses been used extensively in recent literature, although kinetic studies458 suggest that they react 100–1000 times more slowly than do the corresponding acids. 535 R R N CH2CO2Et N CONHC6H11 N CO2Et N H O N H O N O (221) Ph (222) (223) 1,2-Benzenediamine gave 3-perfluoro(2-isopropoxyethyl)-2(1H)-quinoxalinone 896 (224) [EtO2CC(À ÀO)CF2CF2OCF(CF3)2, EtOH, reflux, 48 h: 77%]. 9. Using a Keto Amide, Nitrile, Acyl Halide, or Related Synthon Keto amides (or thioamides) could participate in cyclocondensations by elimination of the amino or oxo (thioxo) function from the amide (thioamide) grouping according to conditions.
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