ChemInform Abstract: Vinylogous N,N-Dimethylaminomethylenation of 3-[(1-Substituted)ethylidene]-oxindoles with N,N-Dimethylformamide Dimethylacetal.

ChemInform ◽  
2014 ◽  
Vol 45 (38) ◽  
pp. no-no
Author(s):  
Hyun Ju Lee ◽  
Sangku Lee ◽  
Jin Yu ◽  
Jae Nyoung Kim
Keyword(s):  
Dimethylformamide Dimethylacetal

Synthesen mit Nitrilen, LVII [1]. Zur Reaktivität von Aminomethylen-malonsäuredinitrilen gegenüber Aldehyden und Orthoestern / Syntheses with Nitriles, LVII [1]. The Reactivity of Aminomethylene-malononitriles with Aldehydes and Orthoesters

1979 ◽  
Vol 34 (11) ◽  
pp. 1580-1586 ◽  
Author(s):  
Martin Mittelbach ◽  
Hans Junek
Keyword(s):  
Double Bond ◽  
Aromatic Aldehydes ◽  
Dimethylformamide Dimethylacetal

Abstract Condensation of aminomethy lene-malononitrile (1a) with aromatic aldehydes and dimethylformamide-dimethylacetal, resp., leads to benzylidene-malononitriles (2a, b) and to dimethylaminomethylene-malononitrile (2e), resp. A mechanism of this cleavage of a C=C double bond is discussed. Several substituted enaminonitriles (1e-i) are prepared and the reactivity against aldehydes is studied. Thus, condensation of 3-Amino-2-cyano-crotononitrile (1e) with aldehydes leads to 2-amino-4-phenyl-1,3-butadiene-1,1-dicarbo-nitriles (3). 4-Oxo-2-phenyl-1,2,3,4-tetrahydro-5-pyrimidine-carbonitriles (4) are yielded by the reaction of 3-amino-2-cyano-crotonic-carboxamide (1h) and 3-amino-2-cyano-cinnamamide (1i), resp., with aldehydes. Condensation of 1h and 1i with ethyl ortho-formate leads to 3,4-dihydro-4-oxo-pyrimidine-carbonitriles (6).

7H-Imidazo[1.2-a]-und -[1.5-a]azepin-7-one / 7H-Imidazo[1,2-a]-and -[1,5-a]azepine-7-ones

1981 ◽  
Vol 36 (3) ◽  
pp. 383-385 ◽  
Author(s):  
Ulrich Wolf
Keyword(s):  
Dimethylformamide Dimethylacetal ◽  
Wittig Reactions

Wittig reactions of imidazole-2- and 4(5)-carboxaldehyde yield the compounds 3 and 4. These vinyl ketones react with N,N-dimethylformamide-dimethylacetal to produce the eneamino-ketones 5 and 6, which are converted into the imidazo-azepine-7-ones (7) and 8.

Reactivity Studies on a Novel 4-(2-hydroxyphenyl)-1,3-dihydro-1,5-benzodiazepine-2-thione

2005 ◽  
Vol 2005 (4) ◽  
pp. 257-261 ◽  
Author(s):  
Rafik Gharbi ◽  
Mouna Ben-Youssef ◽  
Marie-Thérèse Martin ◽  
Zine Mighri
Keyword(s):  
The Novel ◽  
Dimethylformamide Dimethylacetal

The novel 4-(2-hydroxyphenyl)-1,3-dihydro-1,5-benzodiazepine-2-thione (4) has been synthesised and used as precursor to the hitherto unreported 7-methylthio[1]benzopyrano[4,3-c][1,5]-benzodiazepine (7). Hydrazinolysis of 4 gave 5-(2-aminophenylamino)-3-(2-hydroxyphenyl)-1H-pyrazole (9) which with excess of N,N-dimethylformamide dimethylacetal formed the 5-(2-hydroxyphenyl-2H-pyrazol-3-yl)-1H-benzimidazole (10).

Kinetics of the reaction of guanyl-O-methylisourea hydrochloride with dimethylformamide dimethylacetal

1986 ◽  
Vol 51 (9) ◽  
pp. 1964-1971
Author(s):  
Jaromír Kaválek ◽  
Josef Panchartek ◽  
Tomáš Potěšil ◽  
Vojeslav Štěrba
Keyword(s):  
Absorption Maximum ◽  
Base Catalysis ◽  
Dimethylformamide Dimethylacetal ◽  
Catalysis Mechanism ◽  
Kinetics Of

The reaction of guanyl-O-methylisourea hydrochloride (IV) with dimethylformamide (V) proceeds in two steps. The first step consists in the reaction of the imidoester with the imidatonium ion formed in a fast pre-equilibrium to give a conjugated system with the absorption maximum at 278 nm. The subsequent slower step consists in the cyclization to 2-amino-4-methoxy-1,3,5-triazine (VI). The rate of the first step is directly proportional to the concentrations of both hydrochloride IV and acetal V. Both the steps involve base catalysis. Mechanism of the whole reaction is suggested on the basis of the kinetic results.

Synthesis and Cytostatic Activity of N-[2-(Phosphonomethoxy)alkyl] Derivatives of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds

2001 ◽  
Vol 66 (10) ◽  
pp. 1545-1592 ◽  
Author(s):  
Antonín Holý ◽  
Ivan Votruba ◽  
Eva Tloušťová ◽  
Milena Masojídková
Keyword(s):  
Cytostatic Activity ◽  
Secondary Amines ◽  
Dimethylformamide Dimethylacetal ◽  
Alkyl Derivatives ◽  
Derivatives Of ◽  
Related Compounds ◽  
Substituted Adenines

N6-Substituted adenine and 2,6-diaminopurine derivatives of 9-[2-(phosphonomethoxy)- ethyl] (PME), 9-[(R)-2-(phosphonomethoxy)propyl] [(R)-PMP] and enantiomeric (S)-PMP series were synthesized by reactions of primary or secondary amines with 6-chloro-9-{[2-(diisopropoxyphosphoryl)methoxy]alkyl}purines (26-28) or 2-amino-6-chloro-9-{[2-(diisopropoxy- phosphoryl)methoxy]alkyl}purines (29-31) followed by treatment of the diester intermediates32with bromo(trimethyl)silane and hydrolysis. Diesters32were also obtained by reaction ofN6-substituted purines with synthons23-25bearing diisopropoxyphosphoryl group. Alkylation of 2-amino-6-chloropurine (9) with diethyl [2-(2-chloroethoxy)ethyl]phosphonate (148) gave the diester149which was analogously converted toN6-substituted 2,6-diamino- 9-[2-(2-phosphonoethoxy)ethyl]purines151-153. Alkylation ofN6-substituted 2,6-diaminopurines with (R)-[(trityloxy)methyl]oxirane (155) followed by reaction of thus-obtained intermediates156with dimethylformamide dimethylacetal and condensation with diisopropyl [(tosyloxy)methyl]phosphonate (158) followed by deprotection of the intermediates159gaveN6-substituted 2,6-diamino-9-[(S)-3-hydroxy-2-(phosphonomethoxy)propyl]purines160-163. The highest cytostatic activityin vitrowas exhibited by the followingN6-derivatives of 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP): 2,2,2-trifluoroethyl (53), allyl (54), [(2-dimethylamino)ethyl] (68), cyclopropyl (75) and dimethyl (91). In CCRF-CEM cells, the cyclopropyl derivative75is deaminated to the guanine derivative PMEG (3) which is then converted to its diphosphate.

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