213212-11-4Relevant articles and documents
A short synthesis of quinazolinocarboline alkaloids rutaecarpine, hortiacine, euxylophoricine A and euxylophoricine D from methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)anthranilates
Mohanta, Pramod K.,Kim, Kyongtae
, p. 3993 - 3996 (2007/10/03)
Reactions of methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)anthranilates with tryptamine at room temperature produced 2-cyano-3-[2-(indol-3-yl)ethyl]-4(3H)-quinazolinones, which underwent cyclization on heating with TFAA/HCl(g) to afford quinazolinocarboline alkaloids rutaecarpine (1a), hortiacine (1b), euxylophoricine A (1c) and euxylophoricine D (1d) in excellent yields.
A Facile Synthesis of 3-Substituted 2-Cyanoqmnazolin-4(3H)-ones and 3-Alkyl-2-cyanothieno[3,2-d]pyrimidin-4(3H)-ones via 1,2,3-Dithiazoles
Lee, Hyi-Seung,Chang, Yong-Goo,Kim, Kyongtae
, p. 659 - 668 (2007/10/03)
The reaction of methyl anthranilate with 4,5-dichloro-l,2,3-dithiazolium chloride (Appel's salt) in the presence of pyridine (2 equivalents) in dichloromethane at room temperature gave methyl N-(4-chloro-5H-l,2,3-dithiazol-5-ylidene)anthranilate (3a) (50% yield), which reacted with sterically less hindered primary alkylamines to give directly 3-alkyl-2-cyanoquinazolin-4(3H)-ones 5 in moderate to good yields. With tertbutylamine, N-(2-methoxycarbonylphenyl)iminocyanomethyl N-(tert-butyl) disulfide 7 and methyl 2-(N-cyanothioformamido)anthranilate (8) were isolated in 33% and 59% yields, respectively. The cyano group of quinazoline 5a (R = CH3) is readily displaced by various nucleophiles to give 2-substituted quinazolinones 11-19, which indicates that compounds 5 can be utilized as starting materials for the synthesis of new 2-substituted quinazolines. Similarly 3-alkyl-2-cyanothieno[3,2,-d]pyrimidin-4(3H)-ones 22 were prepared from methyl 3-[N-(4-chloro-5H-l,2,3-dithiazol-5-ylidene)]-2-thiophencarboxylate (21) in moderate to good yields.
