- A SHORT SYNTHESIS OF RUTECARPINE AND/OR VASICOLINONE FROM 2-CHLORO-3-(INDOL-3-YL)ETHYLQUINAZOLIN-4(3H)-ONE: EVIDENCE FOR THE PARTICIPATION OF THE SPIRO INTERMEDIATE
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A new route to rutecarpine and/or vasicolinone from 2-chloro-4-quinazolone through an acid catalyzed cyclization of 2-chloro-3-indolylethylquinazolin-4-one has been developed and the mechanism of the cyclization reaction clarified.
- Kaneko, Chikara,Chiba, Takuo,Kasai, Kouichi,Miwa, Chiemi
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p. 1385 - 1390
(2007/10/02)
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- ONE POT SYNTHESIS OF QUINAZOLINE DERIVATIVES BY USE OF PALLADIUM CATALYZED CARBONYLATION
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One pot synthesis of quinazoline derivatives from a mixture of o-iodoaniline 1a and five membered lactams or N-acyl-o-iodoaniline derivatives, 1b and 1c, and primary amines was effected through the palladium-catalyzed insertion of carbon monoxide.
- Mori, Miwako,Kobayashi, Hiromi,Kimura, Masaya,Ban, Yoshio
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p. 2803 - 2806
(2007/10/02)
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- Studies of Rutaecarpine and Related Quinazolinocarboline Alkaloids
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Quinazolinocarboline alkaloids, e.g., rutaecarpine (1), can readily be synthesized by treating tryptamine with 2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one (quickly generated in situ from trifluoroacetic anhydride (TFAA) and 2H-3,1-benzoxazine-2,4(1H)-dione.The product formed, 3--2-(trifluoromethyl)-4-(3H)-quinazolinone (5), is then cyclized (HCl/HOAc) to 13b-(trifluoromethyl)-13b,14-dihydrorutaecarpine (6), whereupon CF3H is eliminated by treatment with base.The sequence can conveniently be performed as a three-reaction one-pot procedure giving rutaecarpine (1) in 99percent yield within 3h.The approach can readily be extended to the synthesis of evodiamine (2), 13,13b-dehydroevodiamine (38a), and 13b,14-dihydrorutaecarpine (21).Thus treatment of 3--4(3H)-quinazolinone (19) with TFAA affected cyclization to 13b-(trifluoroacetyl)-13b,14-dihydrorutaecarpine (20), which can be readily hydrolyzed to 13b,14-dihydrorutaecarpine (21).
- Bergman, Jan,Bergman, Solveig
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p. 1246 - 1255
(2007/10/02)
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