By David T. Davies
Heterocyclic compounds are of major significance to natural chemists operating within the chemical undefined, and heterocyclic chemistry is for this reason a basic subject in undergraduate chemistry classes. The emphasis of this brief textual content is on man made facets, instead of houses, and it covers the fundamental info and easy ideas as regards to the entire vital sessions of heterocyclic compounds. tutorial difficulties are integrated as an relief to comprehension, and references to extra precise texts are supplied.
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Additional info for Aromatic Heterocyclic Chemistry
NH3 I (| ^ HN(CH 2 CHCH 2 ) 2 CI CI Na® 0 SEt H 2 NNH 2 "N' ^ci "~N-NH2 H H,NMe N SEt CI 1 "N ^n' CI HNPh H,NPhs> rf N NMe H N N' CI HN-™2 N' "N © © Na OMe i> N ci N OMe F i n a l l y , b e f o r e l e a v i n g t h i s s e c t i o n , w e s h a l l c o n s i d e r t h e s y n t h e s i s of pyridotriazine 5 . 3 2 , a potential anti-fungal drug. This synthesis illustrates f e a t u r e s of b o t h e l e c t r o p h i l i c a n d n u c l e o p h i l i c p y r i d i n e c h e m i s t r y . N i t r a t i o n of 4 - p y r i d o n e 5 .
T h e y exist exclusively in the p y r i d o n e f o r m , the h y d r o g e n a t o m b e i n g a t t a c h e d to the n i t r o g e n a t o m , n o t the o x y g e n . 23a. OH o B o t h p y r i d o n e s can react with electrophiles at positions ortho a n d para to the activating oxygen atom. 24. 25. W e shall see the utility of 2- and 4 - c h l o r o p y r i d i n e s in the n e x t section. 4 Nucleophilic substitution of pyridines P y r i d i n e c a n b e a t t a c k e d b y n u c l e o p h i l e s at t h e C 2 / C 6 a n d C 4 p o s i t i o n s in a m a n n e r a n a l o g o u s t o t h e a d d i t i o n o f n u c l e o p h i l e s to a c a r b o n y l g r o u p in a 1,2 o r 1,4 f a s h i o n .
29. This pyridone-chloropyridine conversion activates the system to nucleophilic attack by hydrazine, affording 5 . 3 0 . T h e n i t r o g r o u p a l s o f a c i l i t a t e s n u c l e o p h i l i c a t t a c k b y d e l o c a l i s a t i o n of n e g a t i v e c h a r g e in t h e i n t e r m e d i a t e . 29 N-Acylation, reduction HN N. 30 of nitro to a m i n o , and c o n d e n s a t i o n produce d i h y d r o t r i a z i n e 5 . 3 1 . 32. N o t e h o w relatively s i m p l e c h e m i s t r y c a n b e u s e d to f o r m a q u i t e c o m p l e x h e t e r o c y c l e .