Orthophosphoric acid has been found to accomplish the previously unsuccessful oyclization of azomethines of 3-formylcarbazoles and aminoacetal to substituted pyrido[4,3-b]carbazoles according to a scheme proposed by Cranwell and Sexton. By this method, there have been prepared 6,ll-dimethyl-(ellipticine), 5,6,11trimethyl-, 5,9,11-trimethyl-, 9-methoxy-5,ll-dimethyl-(9-methoxyellipticine), 9-methoxy-5,6,11-trimethyl-, 9-bromo-6,ll-dimethyl-, and 9-nitro-5,ll-dimethyl-6H-pyrido[4,3-blcarbazole.
Cyclodehydration in
orthophosphoric acid of the azomethines of 3- formyl-carbazoles and
aminoacetals has yielded 5-methyl- (IId), 3,5,11-
trimethyl-(11b), 3,5,9,11-tetramethyl-(IIc), and
5,7,10,11-tetramethyl- 6H-pyrido[4,3-b]carbazoles (IIa).
In the same way γ-carboline and 6,9- dimethyl-γ-carboline were
obtained from the azomethines of 3-formyl- and 3-formyl-4,7-dimethyl-indole. A Doebner reaction with 3-amino-2- methylcarbazole, acetaldehyde,
and pyruvic acid yielded 1-carboxy-3,5- dimethyl-7H-pyrido[2,3-c]carbazole (VIIIb) from which was derived the methyl ester (VIIIc) and 3,5-dimethyl-7H-pyrido [2,3-c]carbazole (VIIIa).
Various 1,1-dialkylhydrazines
are alkylated by propiolic acid or 2- or 3-halopropenoic acids to give
(E)-3-(1,1-dialkylhydrazin-1- io)propenoates. ��� 3-Bromopropionic acid reacts with
N-aminomorpholine to give 1-amino-1-(2-carboxyethyl)-morpholinium bromide (11),
with N- aminopiperidine to give
bis(1-aminopiperidinium) 2-oxo-1-aza-5- azoniaspiro[4,5]decane
tribromide (10), with 1,1-diethylhydrazine to give 1,1-diethyl-3-oxopyrazolidinium
bromide (9) while with 1,1- dimethylhydrazine the 1 :
1 adduct of 3-(1,1-dimethylhydrazin-1- io)propionate
(5a) and 1-(2-carboxyethyl)-1,1-dimethylhydrazinium bromide (8a) is obtained.
The reaction of 1,1-dimethylhydrazine with methyl propiolate, methyl propenoate
and itaconic acid gives (1,1- dimethylpyrazol-1-ium)-3-olate (4),
(1,1-dimethyl-2-pyrazolin-1-ium)-3- olate (1a) and
(1,1-dimethyl-3-oxopyrazolidin-1-io-4-yl)acetate (7) respectively. 1,1-Dimethylhydrazine
reacts with ethyl 3-bromopropionate to give both 1-(2-ethoxycarbonylethyl)-1,1-dimethylhydrazinium
bromide (8b) and (1,1-dimethyl-2-pyrazolin-1-ium)-3-olate (1a) while its
reaction with bromoacetic acid gives the 1 : 1 adduct of (1,1- dimethylhydrazin-1-io)acetate
(5b) and 1-carboxymethyl-1,1- dimethylhydrazinium
bromide (8c).
2-(1?-Ethoxyethylidene)indandione
(4) and formamidine react to give 4- methyl-5H-indeno[1,2-d]pyrimidin-5-one
(5a). Similarly 2-methyl-(5b), 2-trichloro-methyl- (5c), 2-trifluoromethyl- (5d),
2-amino- (5e), and 2-methylthio-4-methyl-5H-indeno[1,2-d]pyrimidin-5-one (5f)
have been prepared using the respective amidines, guanidine, or
methylisothiourea. Urea and thiourea failed to react and gave instead molecular
addition compounds. ��� 2-Hydroxymethyleneindan-1-one
(6) with urea or thiourea reacts to give the 2-(ureidomethylene)-(7a) or 2-(thioureidomethylene)-indan-1- one
(7b). All attempts to cyclize these compounds to give pyrimidines failed. ��� The alkaline hydrolysis and bromination of
the indenopyrimidines have been investigated.
Die Dialkylhydrazine (I) werden mit verschiedenen ungesättigten bzw. gesättigten Säuren bzw. Estern (II), (V), (VI), (VIII) bzw. (XII) unter Bildung der jeweils angegebenen Produkte umgesetzt.
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