2.4- Dimethyl-3- benzodiazepine

Chemical Name 11 -Chloro-B,12b-dlhydro-2,B-dimethyl-12b-phenyl-4H-[1,3] -oxazlno-[3,2-d] [1,4] benzodiazepine-4,7 (6H)-dione... 

Dimethyl sulfate attacks the sulfur atom in the benzodiazepinethionc 33 to form the 2-(methyl-sulfanyl)-3//-l,4-benzodiazepine 34 in high yield.228... 

Chloro-5-(2-fluorophenyl)-I,3-dimethyl-2-(inethylsulfanyl)-li/-l,4-benzodiazepine (35a) Typical Procedure 230... 

Chloro-5-(2-fluorophenyl)-l,3-dimethyl-l//-l, 4-benzodiazepine-2(3//)-thione (3.3 g, 10 mmol) in DMF (15 mL) was treated with 4.23M NaOMe in MeOH (4.8 mL, 20 mmol). After 30 min, the mixture was cooled in ice and Mel (2.8 g, 20 mmol) was added dropwisc with stirring. After 16 h at 20 C. the mixture was poured into H20 (150 mL) and the precipitated solid was collected and dissolved in CH2Cl2 (75 mL). The solution was washed with dil aq K2C03, dried (Na2S04) and evaporated under reduced pressure. The residue was twice crystallized from MeOH to give the product yield 2.6 g (74%) orange prisms mp 149-152 C. 

Dimethyl-3/7-l, 5-benzodiazepine is methylated at position 3 under basic conditions to give... 

The methyl groups of 2,4-dimethyl-3//-l, 5-benzodiazepine are CH acidic reaction with benzal-dehyde gives a mixture of mono- and distyryl derivatives 13 and 14.256... 

Only one procedure has been reported recently within this category. Thus 7-chloro-l-methyl-5-phenyl-2,3-dihydro-lH-benzodiazepin-2-one 4-oxide (437) with dimethyl acetylenedicarboxylate in methylene chloride at 20° C for 3 days gave a separable mixmre of the primary tricyclic adduct, dimethyl lO-chloro-6-oxo-llb-phenyl-5,6,7, 1 lb-tetrahydroisoxazolo[2,3-t/] [ l,4]benzodiazepine-1,2-dicarboxylate (438), and its rearrangement product, 6-chloro-4-(2-methoxalyl-2-methoxycarbonyl-l-phenylvinyl)-l-methyl-3,4-dihydro-2(lT0-quinoxalinone (439) each product afforded 6-chloro-l-methyl-2(l//)-quinoxalinone (440) on refluxing in ethanol (see also Section 1.7.13). However, the final quinoxaline (440) was best obtained in 75% yield) by simply heating the initial substrate (437) and dimethyl... 

Dimethyl-1,5-benzodiazepine, formulated as its 3H tautomer (445), underwent vapor-phase pyrolysis (850°C, 0.02 mmHg, 15 min) to give a mixmre from which three quinoxalines were isolated 2,3-dimethyl- (446, R = Me) (7%), 2-ethyl-3-methyl- (446, R = Et) (10%), and 2-methyl-3-vinylquinoxa-line (447) (1%). ... 

An analogous substrate, dimethyl 10-chloro-7-methyl-6-oxo-l lb-phenyl-5,6,7,1 lb-tetrahydroisoxazolo[2,3-d][l,4]benzodiazepine-l,2-dicarboxylate (566), gave not 567 but 6-chloro-l-methyl-2(l/7)-quinoxalinone (EtOH, reflux, 30 h -40%). ... 

CN ll-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyI-4//-[l,31oxazino[3,2-i/][l,4]benzodiazepine-4,7(6//)-dione... 

Further new competitive AMPA antagonists include the imidazo-fused 23-benzodiazepine derivative 103. This compound showed excellent anticonvulsant activity and other activities indicative of possible therapeutic significance in human stroke and Parkinson k disease <00BMC2127>. An efficient synthesis of fluorine-containing H-1,4-diazepino[6,5-/t]quinolines has been described based on iV,/V-dimethyl-5,7-bis(trifluoroacetyl)-8-quinolylamine and an aromatic nucleophilic displacement with 1,2-ethylenediamine, followed by cyclocondensation <00S1822>. 

Dimethyl malonate was reacted with 2-(iV-nitrosomethylamino)-1,4-benzodiazepines (502, R = H, F n = 0, 1) in the presence of potassium tm-butoxide in DMF under nitrogen to give (1,4-benzo(6)diazepin-2-ylidene)malonates (503, R = H, F n = 0, 1) (75JOC153 83USP4401597). A dichloro derivative of (1,4-benzodiazepin-2-ylidene)malonate (503, R = Cl, = 0) was prepared in the reaction of a 1,4-benzodiazepine derivative (504) and dimethyl malonate under the previous conditions (83USP4401597). 

The dimethyl-1,5-benzodiazepine 43 on attempted nitration with H2S04-HN03 at 0°-5° gave, by ring contraction, 2-acetyl-3-methyl-quinoxaline (26%), together with some of the AVV -diacetyl derivative of 1,2-diamino-4-nitro benzene.44... 

A solution of 0.7 g of 2-(2-amino-N-methylacetamido)-5-chlorobenzophenone in 10 ml of a 50% solution (by weight) of diketene in acetone is refluxed for 3 hours and then evaporated to give a brown oil. The oil is chromatographed on 200 g of silica gel using a 1 1 (by volume) mixture of ethyl acetate cyclohexane 25 ml fractions are collected. Fractions 11-14 are combined, mixed with chloroform, evaporated and triturated with ether to give 0.337 g of ll-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4H-[l,3]oxazino[3,2-d] [1.4] benzodiazepine-4,7(6H)-dione as a pale yellow solid, MP 174°C to 176°C. 

Chemical Name 4,9-Dihydro-l,3-dimethyl-4-[(4-methyl-l-piperazinyl) acetyl]pyrazolo[4,3-b][l,5]benzodiazepin-10-(lH)-one... 

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