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3- perhydropyrido

Acetyl-3-(perhydropyrido[l, 2-u]pyrazin-2-yl)-1 //-indole was deacety-lated in boiling MeOH in the presence of NaOH, and the product, 3-(perhydropyrido[l,2-u]pyrazin-2-yl)-l//-indole was N-acylated with different arylsulfonyl chloride in THF at 0°C in the presence of (Me3Si)2NNa (99MIP12, 01USP6251893)). [Pg.308]

Reduction of 3-benzyl-8-chloro-4-oxo-4//-pyrido[l,2- ]pyrimidine-2-carboxylate <2004W004/064741> and 2-methyl-4-oxo-4//-pyrido[l,2-tf]pyrimidine-3-carboxylate <2003T4123> with DIBAL-H afforded 2- and 3-formyl derivatives, respectively. Reduction of /V-(4-fluorobenzyl)-3-hydroxy-8-[methoxy(methyl)amino]-4-oxo-6,7,8,9-tetra-hydro-4//-pyrido[l,2- ]pyrimidine-2-carboxamide with Zn-dust in aqueous AcOH afforded the 8-methylamino derivative, which was acylated with AcOH in the presence of Hiinig s base, HOBt, and l-(3-dimethylaminopro-pyl)-3-ethylcarbodiimide-HCl <2004W004/058756>. 3-(Perhydropyrido[l,2- ]pyrimidin-2-yl)propylamine was obtained by catalytic hydrogenation of 2-(perhydropyrido[l,2- ]pyrimidin-2-yl)propionitrile over a Pt02 catalyst <2003FRP1275647>. [Pg.171]

The perhydropyrido[2,l-Z)][l,3]oxazine skeleton is a constituent part of macrocyclic xestospongine/araguspongine and aragupetrosine alkaloids... [Pg.175]

Molecular mechanics calculations with the molecular mechanics force field program were performed to compare thermodynamic stability among araguspongine B (17) (containing two cw-fused perhydropyrido[2,l-Z>] [l,3]oxazine bicycles), araguspongine D (18) (containing two tran -fused perhydropyrido[2,l-Z)][l,3]oxazine bicycles), and araguspongine E (19)... [Pg.177]

Enantiopure (7 )-3-alkylpiperidines (38, R = Me, Et) were obtained when perhydropyrido[2,l-Z)][l,3]benzoxazin-9-ones (37, R = H, Me) were treated first with an excess of AIH3, then with PCC, followed by a 2.5 N solution of KOH (99TL2421). Treatment of optically active perhydropyr-ido[2,l-Z)][l,3]benzoxazines 39 and 40 with LAH in the presence of AICI3 and DIBALH (if R = COOEt) yielded 3-substituted piperidines 41 (00TA2809). [Pg.182]

Radical cyclization of perhydro-l,3-benzoxazines 64, promoted by Bu4SuH in the presence of AIBN gave a mixture of perhydropyrido[2,l-6][1,3]benzoxazin-9-ones 65 and 66 and seven membered tricyclic derivatives 67 and 68, formed in a 6-exo and 7-endo cyclization process, respectively (99TL2421). Cyclization of parent acrylamide 64 (R = R = H) occured with moderate regioselectivity (6-exo/7-endo ratio 65 35) and poor stereoselectivity (65/66 ratio 42 43). The presence of a /3-methyl group in... [Pg.186]

Diastereoseleetive 6-exo-trig radieal eyelization of (-)-perhydro-l,3-benzoxazines 69, 71, 74 with Bu3SnH and AIBN gave a diastereomerie mixture of perhydropyrido[2,l-Z)][l,3]-benzoxazines 39, 70, and 72, 73, and 40, 75, respeetively (00TA2809). [Pg.187]

Chiral 3-alkylpiperidines were prepared through perhydropyrido[2,I-Z)][],3]benzoxazines (99TL242I, 00TA2809). 5u-Pentyl-5u,6,7,8,9,H-hexa-hydropyrido[2,I-Z ][l,3]benzoxazin-9-ones 31, 33 (R CsHn) and 34 were used in the total synthesis of racemic and natural (—)-(R) forms of adalinine alkaloid (99SL37, 99TL739). [Pg.189]

Perhydropyrido[l,2-a]pyrimidin-2-one was A -alkylated with 1,4-dibro-mobutane to yield a 1-(4-bromobutyl) derivative (94MIP6). 6-Methyl-4-oxo-4/f-],6,7,8,9,9a-hexahydro-4//-pyrido[],2-a]pyrimidine-3-carboxylate 138 was alkylated with alkyl chlorides 139 to give 1-substituted derivatives 140 (97MIP2). [Pg.205]

Reaction of perhydropyrido[l, 2-n]pyrimidine with BrCN in the presence of MgO in a 1 1 mixture of CHCI3 and MeOH at 40 °C resulted in the formation of the ten-membered 6-methoxy-3,4,7,8, 9,10-hexahydro-l,5-diazecine-l,5-(2//,6//)-dicarbonitrile. Similar reaction of perhydropyrido[l, 2-n]pyrimidin-2-one led to the nine-membered 6-methoxy-4-oxo-2,3,4,5,6,7,8,9-octahydro-l//-l,5-diazonine-l-carbonitrile (99AJC1131). [Pg.233]

Dehydrogenation of piperidine derivative 329 with Hg(II)-EDTA reagent afforded a mixture of perhydropyrido[l,2-n]pyrimidin-2-one 330 and pyrido[],2-c][],2,5]oxadiazine 331 (99ZN(B)632). [Pg.239]

CO were used only perhydropyrido[l,2-u]pyrimidine (398, R = H) formed from compound 397 (R = H). [Pg.252]

Perhydro derivatives of pyrido[l,2-7)][l,2]oxazines are frequently applied in the total synthesis of various alkaloids to control the stereochemistry, and pyrido[l,2-c][l,3]oxazines and [l,3]oxazino[3,4-u]quinolines were also used in the stereoselective syntheses of different alkaloids. Perhydropyrido[l,2-c][l,3]oxazines and their benzologs are formed form 2-(2-hydroxyethyl) piperidines and from their benzologs to justify the stereochemistry of 2-(2-hydroxyethyl) derivatives. Different optically active pipecolic acids can be prepared via 4-phenylperhydropyrido[2,l-c][l,4]oxazin-l-ones. [Pg.224]

Reductive N-O bond cleavage of perhydropyrido[l,2-6][l,2]oxazine 10 with Zn dust furnished 2-(3-hydroxypentyl)piperidine 11 (96JCS(P1)1113). Similarly, 2/S,4u S,5Q ,7/0,8yS-H-5-benzyloxy-7-(tert-butyldiphenylsilyloxy)-2-[2-(methoxymethoxy)ethyl]-8-methylperhydropyrido[l,2-6][l,2]oxazine gave the respective ring-opened piperidine (OOOL2955, 01JOC3338). [Pg.226]

Hydroxy group of perhydropyrido[l,2-A][l,2]oxazin-8-one 23 (R = H) was protected with t-BuPh SiCl in the presence of imidazole in DMF (OOOL2955, 01JOC3338). [Pg.229]

Perhydropyrido[l,2-A][l,2]oxazines are applied as key intermediates in a stereospecific total syntheses of (-)-pumiliotoxin C and 5-e/ /-pumiliotoxin C(96JCS(P1)1113), and the marine alkaloid)—)-lepadins A, B, C (OOOL2955). (2-Pyridyl)propionic acids 13 can be regioselectively prepared via 2,3,4, 4fl,7,8-hexahydropyrido[l,2-A][l,2]oxazin-2-ones 12 (00OL4007). [Pg.231]

Treatment of perhydropyrido[l,2-c][l,3]oxazin-l-ones 83, 85, and 87 with 2M ethanolic KOH afforded 2-(2-hydroxyalkyl)piperidines 84, 86, and 88 (96CJC2434). (4-)-9-Epi-6-epipinidinol (90) was obtained similarly from 3,8-dimethylperhydropyrido[l,2-c][l,3]oxazin-l-one 89 (98T13505). [Pg.240]

Di-(2-propyl)]perhydropyrido[l, 2-c][l, 3]oxazin-l -one was lithiated with 5-BuLi in the presence of TMEDA 200 times less efficiently, than the five-membered lower homolog 3,3-[di(2-propyl)]perhydropyrido[l,2-c][l,3] oxazolin-l-one, and approximately five times more efficiently than -(tert-butoxycarbonyl)piperidine (01JA315). [Pg.241]

Methyl-3-(tosyloxymethyl)perhydropyrido[l,2-c][l,3]oxazin-l-one 103 was detosylated by treatment with LiBEt3H (Super-Hydride ) (98T13505). [Pg.242]

Substituted perhydropyrido[l,2-c][l,3]oxazines 83 were obtained by the cyclization of l-(/er/-butoxycarbonyl)-2-(2-hydroxyalkyl)piperidines 104 in pyridine on the action of MeS02Cl at room temperature (96CJC2434). Cyclization of c/5-2,6-H- l-(methoxycarbonyl)-2-(2-acetoxyhexyl)-9-methox-ypiperidines 105 and 106 in THF in the presence of KO/-Bu yielded 3-butyl-9-methoxyperhydropyrido[l,2-6 ][l,3]oxazin-l-ones 94. Treatment of l-(/erc-butoxycarbonyl)-2-[2-hydroxy-2,2-di(2-propyl)ethyl]piperidine with NaH in boiling THF yielded 3,3-di(2-propyl)perhydropyrido[l,2-c][l,3] oxazin-l-one (01JA315). [Pg.243]


See other pages where 3- perhydropyrido is mentioned: [Pg.178]    [Pg.179]    [Pg.191]    [Pg.234]    [Pg.228]    [Pg.243]   
See also in sourсe #XX -- [ Pg.2 , Pg.4 ]

See also in sourсe #XX -- [ Pg.2 , Pg.4 ]

See also in sourсe #XX -- [ Pg.2 , Pg.4 ]

See also in sourсe #XX -- [ Pg.2 , Pg.4 ]




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2- Substituted-7- perhydropyrido pyrazine

2- carbonyl perhydropyrido

2- perhydropyrido pyrazin-3-one

2- perhydropyrido pyrazine

2- propionate perhydropyrido pyrimidine-1,3dione, acid hydrolysis

3- Alkoxy-2- perhydropyrido oxazines

3- Hydroxy-3- perhydropyrido oxazine

3- perhydropyrido oxazine

3.3- perhydropyrido oxazin-l-one, lithiation

4- Phenyl-9- perhydropyrido oxazin-l-one

4- Phenyl-9- perhydropyrido oxazin-l-one catalytic hydrogenation

4- perhydropyrido oxazines, reaction with

4- perhydropyrido pyrimidine

6- perhydropyrido pyrazines

6-Formyl-2- perhydropyrido pyrazine

7- Hydroxymethyl-2- perhydropyrido

7-Hydroxyethyl-2- perhydropyrido pyrazines

8-Methyl-3- perhydropyrido oxazin-l-one

9 perhydropyrido oxazin-1-ones, reduction

Perhydropyrido [! ,3)thiazines

Perhydropyrido benzoxazines

Perhydropyrido oxazin1,3,5-triones

Perhydropyrido oxazine, dipole

Perhydropyrido oxazine, dipole moments

Perhydropyrido oxazine-3,6-dione

Perhydropyrido oxazines

Perhydropyrido pyrazine-3,4-dione

Perhydropyrido pyrazine-4-ones

Perhydropyrido pyrazines preparation

Perhydropyrido pyrazines reactions

Perhydropyrido pyridazine

Perhydropyrido pyrimidine, Bohlmann

Perhydropyrido pyrimidine, ring

Perhydropyrido thiazin-4-ones

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