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Pyrimido isoquinolines

In the case of the 2-dimethylamino- (or 2-amino-)methylene derivatives, the products were at first thought to be pyrimido[4,5-c]isoquinolines (267), but later work with 6-(N-substituted amino)uracils assigned the structures of the products (268) as belonging to the isomeric pyrimido[4,5-f>]quinoline system (74CB2537), in agreement with the regioselection rules above. [Pg.231]

Catalytic debenzylation of 10-(dibenzylamino)-6-(4-rerr-butylphenyl)-3,4-dihydro-2//-pyrimido[2,l-n]isoquinoline 421 (R = PhCH2) over a 5% Pd/C catalyst under hydrogen at atmospheric pressure in acidified EtOH at ambient temperature afforded the 10-amino derivative 421 (R = H) (98JMC1050). [Pg.260]

Lithiation of 2-(2-alkylphenyl)-l,2,3,4-tetrahydropyrimidines 427 with 1.3 M BuLi in the presence of A/, A/, A, A -tetramethylethylenediamine, then with 1.3 M -BuLi, followed by the addition of a carboxylic acid methyl ester, and treatment of the reaction mixture with pTSA afforded 3,4-dihydro-2/f-pyrimido[2,l-u]isoquinolines 428 after chromatographic work-up (98JMC1050). [Pg.263]

Fluorophenyl)-l ]-hydroxy-2,3,4,1 ]-tetrahydro-6/7-pyrimido[],2-Z)]-isoquinolin-6-one was obtained in the reaction of l-(4-fluorophenyl)-3-oxo-],3-dihydro-2-benzofuran-l-carboxamide and 1,3-diaminopropane in boiling toluene (01BMCL339). [Pg.265]

The use of 1 l//-pyrido[2,l-Z)]quinazolin-l 1-ones in an organic electroluminescent device was patented (99JAP(K)99/74080). 2//-Pyrimido[2,l-n]isoquinolin-7-ols were patented as multi-functional fuel and lube additives (97USP5646098). [Pg.266]

Conformational studies of c/5-6,11/)-H- and /rnns-6,ll/)-H-6-methyl-2,3,4,6,7,1 l/)-hexahydro-l//-pyrimido[6,l-n]isoquinolin-2-ones (136 and 137) by means of the MM2 method implemented in the HyperChem 4.5 suggested, that in the lowest-energy conformations heterocyclic moiety adopted trans-fu ed ring annotation in both cases, with a pseudo-equatorial and -axial methyl group, respectively (97LA1165). [Pg.247]

The mass spectral fragmentations of 9,10-dimethoxy-2,3,4,6,7,ll/)-hexa-hydro-l//-pyrimido[6,l-n]isoquinolin-2-ones 140 and -2,4-diones 141, under electron ionization (at 70 eV) were examined by metastable ion analysis, a collosion-induced dissociation technique and exact mass measurement (97RCM1879). Methyl substituent on N(3) in 140 (R = Me) had a larger effect on both the fragmentation and on the peak intensities, than a methyl substituent on C(6) (R = Me). The ionized molecules of 140 (R = H) were rather stable, whereas 4-phenyl substitution on C(4) of 140 (R = Ph) promoted the fragmentations of the molecular ions. The hexahydro-1//-pyrimido[6,l-n]isoquinoline-2,4-diones 141 were more stable, than the hexahydro-l//-pyrimido[6,l-n]isoquinolin-2-ones 140, and the molecular ions formed base peaks. [Pg.248]

Heating 3-hydroxymethyl derivative of epimeric 6-methyl-l,3,4,6,7,l l/>-hexahydro-2//-pyrimido[6,l-n]isoquinolin-2-ones 151 resulted in the formation of 3-unsubstituted derivatives 152 by loss of CH2O (97LA1165). [Pg.252]

Reaction of 2-chloro-6,7-dihydro-4//-pyrimido[6,1 -a]isoquinolin-4-ones with liquid NH3 in a pressure bomb at 85 °C for 4h, and with primary and secondary amines in boiling CHCI3 (98MIP15), and anilines in boiling i-PrOFI (00MI17) yielded 2-amino-6,7-dihydro derivatives or their 2,3,6,7-tetrahydro-2-imino tautomers. [Pg.253]

Aryloxy-9,10-dimethoxy-6,7-dihydro-4//-pyrimido[6,1 -a]isoquinolin-4-ones formed in the reaction of 2-chloro derivative and phenols in the presence of K2CO3 in DMF at 90 °C for 2. 5 h or in boiling 2-PrOH for 6-24 h (00MIP20). When 2-isobutylphenol was used the reaction was carried out in the presence of BuLi in THF at —78 °C. [Pg.254]

Cyclocondensation of a-aryl-2-pyridylacetamides and 2-(3,4-dihydroiso-quinolin-l-yl)acetamide with Et2C03 in the presence of NaOEt in boiling EtOH afforded 4-aryl-2,3-dihydro-l//-pyrido[l,2-c]pyrimidine-l,3-diones (99JHC389) and 6,7-dihydro-4//-pyrimido[6,1 -a]isoquinoline-2,4-dione (98MIP15), respectively. [Pg.259]

Reactions of 3-methyl-1,2,3,4-tetrahydroisoquinoline-1-acetamides 202 (R = H) with 36% aqueous CH2O at 60 °C gave 1,3,4,6,7,1 Ih-hexahydro-2//-pyrimido[6,l-a]isoquinolin-2-ones 152 and their 3-methyl derivatives (97LA1165). When the reaction was carried out in the presence of 37% aqueous NaOH 3-hydroxymethyl derivatives 151 were obtained. Reactions with PhCHO were stereospecific to afford only diastereomers 203. [Pg.260]

N Pyrimido[1,2-6]isoquinoline Pyrimido[2,1 -bjquinazoline Pyrrimido[2,1 -ajisoquinoline... [Pg.82]

Cyclization occurred at the N-3 atom when 4-(3-bromopropylaruino)-l, 6,7,1 1 b-tctrahydro-2//-pyrimido[6,l -zz -isoquinoline was treated with NaH to give a tetracyclic derivative <2003M1271>. 9,10-Dimethoxy-2-(arylimino)-2,3,6,7-tetrahydro-4//-pyrimido[6,l- ]isoquinolin-4-ones were N-3-alkylated with iV-(ra-bromoalkyl)phthalimides in the presence of K2C03 and a catalytic amount of I2 in boiling 2-butanone in 13-67% yields <2000W020/058308>. Treatment of the 2-[(4-methoxyphenyl)methyl] derivative of 2,3,6,7-tctrahydro-l //,5//-pyrido[3,2,l-/ylqninazolinc-... [Pg.100]


See other pages where Pyrimido isoquinolines is mentioned: [Pg.224]    [Pg.227]    [Pg.231]    [Pg.231]    [Pg.810]    [Pg.176]    [Pg.266]    [Pg.222]    [Pg.249]    [Pg.252]    [Pg.254]    [Pg.256]    [Pg.256]    [Pg.81]    [Pg.81]    [Pg.95]    [Pg.95]    [Pg.96]    [Pg.99]    [Pg.100]    [Pg.103]   
See also in sourсe #XX -- [ Pg.62 ]




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2- -6,7-dihydro-4//pyrimido isoquinolin-4-ones

3,3-Diethyl -3,4-dihydro-277-pyrimido isoquinoline-2,4-dione

3- Hydroxy-3,4,6,7-tetrahydro-2//pyrimido isoquinolines

3.4- Dihydro-2//-pyrimido isoquinoline-2,4-diones

4- pyrimido

6- -3,4-dihydro-2//pyrimido isoquinoline, inhibition

6.7- Dihydro-2//-pyrimido isoquinolines, catalytic reduction

6.7- Dihydro-477-pyrimido isoquinoline-2,4-dione

9.10- Dimethoxy-2,3,6,7-tetrahydro-4//pyrimido isoquinoline-2,4-dione

9.10- Dimethoxy-2- -6,7-dihydro-4//-pyrimido isoquinolin-4-one

9.10- Dimethoxy-3,4,6,7-tetrahydro-2 pyrimido isoquinolin-2,4-dione

Pyrimido isoquinoline-3-carboxylates

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