By Desmond J. Brown, Edward C. Taylor, Peter Wipf
This quantity within the Chemistry of Heterocyclic Compounds sequence provides a finished evaluate of the quinoxaline literature from 1975 to the current (2002), updating Volumes five and 35. It offers an alphabetical desk of recognized uncomplicated quinoxalines, together with new compounds mentioned during this quantity and their actual info, in addition to the pyrazines from the unique volumes. organic actions, spectral or different actual stories, and different such fabrics look at acceptable issues within the textual content. The in-depth insurance contains synthesis, reactions, spectroscopic, and actual homes for every type of compounds.Chemistry of Heterocyclic Compounds, quantity sixty one: complement II offers the main updated summation of data of the artificial chemistry of quinoxalines.
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This quantity within the Chemistry of Heterocyclic Compounds sequence offers a finished evaluation of the quinoxaline literature from 1975 to the current (2002), updating Volumes five and 35. It offers an alphabetical desk of recognized basic 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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Additional info for Quinoxalines.Supplement II
911,cf. 914,cf. 4. Isothiazoles as Substrates/Synthons Although of more interest than utility, the desulfurization of certain isothiazoles with triphenylphosphine leads to separable mixtures from which quinoxalines have 50 Primary Syntheses been isolated in low yield. 5. Isoxazoles as Substrates/Synthons Although little used, this type of synthesis may be employed in two different ways to produce quinoxalines from o-phenyldiamines as substrates. Examples follow.
Such isomers are usually separable but often with considerable loss. Mainly to avoid this situation by achieving regioselectivity in syntheses, a variety of aldehydo ketone equivalents have been employed as synthons but with mixed results. The following classified examples illustrate the generalities mentioned above. 551 From a Benzene Substrate with an Ancillary Synthon Cl NH2 Cl NH2 O + O (110) CPh CH Cl N Cl N (111) 19 Ph (112) 1,2-Benzenediamine gave 2-(2,4-dimethylphenyl)quinoxaline (113) [2,4826 Me2C6H3C(À or 2-(40 -acetoxybiÀO)CHO, AcOH, 100 C, 30 min: 55%] phenyl-4-yl)quinoxaline (114) (p-AcOC6H4C6H4COCHO-p, EtOH, reflux, ?
FROM A PYRAZINE SUBSTRATE WITH OR WITHOUT SYNTHON(S) This potentially wide category of primary syntheses remains almost unutilized apart from the few examples here given. 90 C, 15 min: 38%); prop-1-ynylbenzene or 1-ethynylnaphthalene likewise gave 6-methyl-7phenylquinoxaline (43%) or 6-(naphthalen-1-yl)quinoxaline (41%), respectively,1112 Br2HC N hν, NaI BrHC N PhC CH Ph N ? 5. FROM OTHER HETEROMONOCYCLIC SUBSTRATES/SYNTHONS Heteromonocyclic compounds other than pyrazines may be used as substrates or synthons for the primary synthesis of quinoxalines.