Chemistry. — " The Si/uthesis 0/ some Pi/rult/lpyi-roles." Bj Dr. 

 J. P. WiBAi'T and Miss Elisabeth Dinghmanse. (Communicated 

 by Prof. P. VAN Rombuhgh.) 



(Communicated at the meeting of March 24, 1923.) 



In the course of the researclies on the structure of the natural 

 alkaloids, several of these vegetable bases have been prepared by 

 synthesis. In other groups of vegetable substances, investigatoi's have 

 not only sncceeded in building up the substances occnning in nature, 

 but also closely allied bodies were obtained synthelically. In Ihe 

 group of Ihe sugars, e.g., a number of monoses have been oblained 

 which do not occur in the vegetable kingdom, l)ut which are 

 isomeric with or closely related to the sugars fonnd in nature. Our 

 knowledge of the chemical and l)i()chemical properties of the monoses 

 Jias been greatly improved by these synthetic researches. It seems 

 not devoid of interest to try and build up an isomer of a natui-al 

 alkaloid, in order to examine afterwards in what lesjiect the iso- 

 meric substance is distinguished from llie nalnial alkaloid, especially 

 with regard of physiological and biochemical properties. 



Keeping this end in view we will try to build up an isomer of 

 nicotine. 



' In his synthesis of nicotine Pictet started from |?-amino-pyridine; 

 this substance was heated with mucic acid, through which N (/?- 

 pyridyl)-pyrrole (I) was oblained. At high lem|)erature N (|J-pyridyl) 

 pyrrole undergoes an isomerisalion, in which C (iJ-pyridyl)-pyrrole 

 (II) is formed : 



CH .CH = CH 



HCf^\|C — N j ^ 



I II ^CH = CH 



HC'^^'CH 



N 



I. 



Pictet and Crépieux ') give the above structure to this C (jJ-pyridyl) 



1) Ber. d. deutsch. chem. Ges. 28, 1904 (1895). 



