Re: ORGLIST:Help on methylation

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From: Santi (santidel$##$um.es)
Date: Thu Jul 03 2003 - 11:34:46 EDT

Hi Srinivas, you can try with the following procedures for the methylation
in the pyridin nitrogen:

1) This procedure was made for the synthesis of an indolo[3,2-c]quinoline:
Me2SO4, MeCN, reflux, 5 h, K2CO3.

2) This procedure was made for the synthesis of an indolo[2,3-b]quinoline:
i) Me2SO4, Toluene, sealled tube, 150ºC ii) NaOH 20%.
                         or Me2SO4, DMF, Microwave, 140ºC, 5 min.

You can have a look these references:

-Iminophosphorane-Mediated Synthesis of the Alkaloids Cryptotackieine.
Molina, P.; Fresneda, P. M.; Delgado, S. Synthesis, 1999, 2, 326.
-Peczynska-Czoch, W.; Pognan, F.; Kaczmarek, L.; Boratynski, J. J. Med.
Chem. 1994, 37, 3503.

-Timári, G.; Soós, T.; Hajós, G. Synlett 1997, 1067.

Good luck

Santi.

At 03:32 03/07/2003 -0700, srinivas reddy wrote:
>Dear All,
>
>I am a research student, trying to synthesize
>indoloquinoline analogues, in one of my reactions I
>have to methylate my substrate.
>
>
>I tried to methylate by using methyl iodide, and
>tetramethylene as the solvent at 60 degree centigrade
>overnight in an inert atmosphere,I also tried with
>methyl triflate and toluene as the solvent,but the
>reaction didnot work. can anybody help me on why the
>reaction didnot work and also the other method for
>methylation?,as this is very important for my project.
>
>I am herewith attaching the structures of my substrate
>and compound.
>
>
>thank you
>
>regards
>
>Srinivas
>
>__________________________________
>Do you Yahoo!?
>SBC Yahoo! DSL - Now only $29.95 per month!
>http://sbc.yahoo.com

____________________________________
   Santiago Delgado Ballester.
   Departamento de Química Orgánica.
   Facultad de Química.
   Campus de Espinardo.
   Universidad de Murcia.
   CP 30100. Murcia. SPAIN.
   Telf: +34-630-440-600
   Telf: +34-968-367493
   Fax: +34-968-364149
   e-mail: santidel$##$um.es
_____________________________________

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