Download e-book for kindle: Aromatic Heterocyclic Chemistry by David T. Davies

By David T. Davies

ISBN-10: 0198556608

ISBN-13: 9780198556602

Heterocyclic compounds are of top value to natural chemists operating within the chemical undefined, and heterocyclic chemistry is accordingly a basic subject in undergraduate chemistry classes. The emphasis of this brief textual content is on artificial features, instead of houses, and it covers the fundamental info and simple ideas with regards to all of the very important periods of heterocyclic compounds. tutorial difficulties are incorporated as an relief to comprehension, and references to extra special texts are supplied.

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Example text

16 HO. 17 The other important isoxazole synthesis involves the concerted [3+2] cycloaddition reaction of nitrile oxides 4 . 1 8 with either alkynes 4 . 20. X=0Ac,NMe 2 ,N0 2 A w i d e r a n g e of n i t r i l e o x i d e s is k n o w n ( R 3 = H , aryl, a l k y l , e s t e r , h a l i d e , etc). 18 Several oxidising agents can be used (lead tetraacetate, N- b r o m o s u c c i n i m i d e , c h l o r i n e , e t c ) . A m e c h a n i s m is i l l u s t r a t e d b e l o w f o r alkaline sodium hypochlorite.

2 1 a n d n i t r o t o l u e n e 7 . 20. 20 H y d r o g e n a t i o n of e n a m i n e 7 . 2 0 r e d u c e s t h e n i t r o g r o u p g i v i n g a n i l i n e 7 . 2 4 , t h e n e l i m i n a t i o n of p y r r o l i d i n e p r o d u c e s i n d o l e 7 . 1 . N o t e t h e s i m i l a r i t y of this r i n g c l o s u r e s t e p t o t h e last s t e p of t h e F i s c h e r s y n t h e s i s . I n b o t h c a s e s t h e e v e n t u a l C 2 c a r b o n a t o m is f o r m a l l y at t h e c a r b o n y l o x i d a t i o n l e v e l , e v e n t h o u g h it o c c u r s as e i t h e r a n i m i n e ( F i s c h e r s y n t h e s i s ) o r a n e n a m i n e ( L e i m g r u b e r s y n t h e s i s ) .

2 6 . A s i m p l i s t i c r a t i o n a l e is s h o w n b e l o w . 26 Aq. g. h a l i d e i o n s i n s t e a d of h y d r i d e i o n s ) are e m p l o y e d . e x ^ x -a! o © e -- 7 x -ci ( h • 3 e •. X = Nucleophile N u c l e o p h i l i c s u b s t i t u t i o n s a r e w i d e l y u s e d in p y r i d i n e c h e m i s t r y . S o m e e x a m p l e s are s h o w n below. 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 .

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Aromatic Heterocyclic Chemistry by David T. Davies


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