19801-37-7Relevant articles and documents
Structures of 1,2,3,4-tetrahydro-6H-pyrimidoquinazolin-6-one and its hydrochloride
Glowka, Marek L.,Olczak, Andrzej,Korzycka, Lucyna
, p. 725 - 730 (1994)
C11H11N3O, m.p. 243 deg C, P2/n, Z = 4, a = 5.843(2), b = 14.241(3), c = 11.102(1) Angstroem, β = 93.30(2) deg, R = 0.046; C11H11N3O*HCl*H2O, Pca21, Z = 8, a = 18.640(2), b = 8.894(2), c = 14.404(2) Angstroem, R = 0.062.The molecules of the free base are in 1H-tautomeric form.N(1)-H...N(11) hydrogen bonds join molecules of the free base into dimers, which enable tautomeric rearrangement (not observed in this study) also in the solid state without any changes in molecular packing.The quinazoline system deviates slightly from planarity and benzene ? electrons are partially localized at C(7)-C(8) and C(9)-C(10) bonds as seen from their lengths of about 1.375 Angstroem, while other bonds in the benzene ring are at least 0.02 Angstroem longer.Key words: Pyrimidoquinazoline, hydrochloride, neuroleptic.
Divergent 2-Chloroquinazolin-4(3H)-one Rearrangement: Twisted-Cyclic Guanidine Formation or Ring-Fused N-Acylguanidines via a Domino Process
Yan, Gang,Zekarias, Bereket L.,Li, Xiaoyu,Jaffett, Victor A.,Guzei, Ilia A.,Golden, Jennifer E.
, p. 2486 - 2492 (2020/02/13)
A highly efficient 2-chloroquinazolin-4(3H)-one rearrangement was developed that predictably generates either twisted-cyclic or ring-fused guanidines in a single operation, depending on the presence of a primary versus secondary amine in the accompanying diamine reagent. Exclusive formation of twisted-cyclic guanidines results from pairing 2-chloroquinazolinones with secondary diamines. Use of primary amine-containing diamines permits a domino quinazolinone rearrangement/intramolecular cyclization, gated through (E)-twisted-cyclic guanidines, to afford ring-fused N-acylguanidines. This scalable, structurally tolerant transformation generated 55 guanidines and delivered twisted-cyclic guanidines with robust plasma stability and an abbreviated total synthesis of an antitumor ring-fused guanidine (4 steps, 55 % yield).
Radical synthesis of guanidines from N-Acyl cyanamides
Larraufie, Marie-Helene,Ollivier, Cyril,Fensterbank, Louis,Malacria, Max,Lacote, Emmanuel
supporting information; experimental part, p. 2178 - 2181 (2010/06/18)
Chemical Equation Presented Center stage: Additions of nitrogen-centered radicals to cyanamide compounds provided the first radical synthesis of aromatic polycyclic guanidine derivatives (see scheme). Modular assembly of the substrates allows for a rapid increase of the molecular complexity of scaffolds, which have potential applications for medicinal chemistry.