Amidrazones. VII . Formation of  s ‐triazines by thermolysis of  N  1 ‐benzyl‐substituted amidrazone ylides | Zendy

Smith Richard F. | Zendy; Soelch Richard R. | Zendy; Feltz Timothy P. | Zendy; Martinelli Michael J. | Zendy; Geer Susan M. | Zendy

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Amidrazones. VII . Formation of s ‐triazines by thermolysis of N 1 ‐benzyl‐substituted amidrazone ylides

Author(s) -

Smith Richard F.,

Soelch Richard R.,

Feltz Timothy P.,

Martinelli Michael J.,

Geer Susan M.

Publication year - 1981

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570180218

Subject(s) - chemistry , dimethylamine , thermal decomposition , benzaldehyde , medicinal chemistry , decomposition , triazine , ylide , organic chemistry , catalysis

The preparation of ylides of the general structureis described. Thermolysis of 14a (R = CH 3 , R' = H, Ar = C 6 H 5 ) gave dimethylamine and 2,4‐dimethyl‐6‐phenyl‐ s ‐triazine. Thermolysis of ylides 14b (R = C 6 H 5 ; R' = CH 3 , Ar = C 6 H 5 ) and 14c (R = C 6 H 5 , R' = CH 3 , Ar = p ‐tolyl) gave dimethylamine, ArCH = NCH 3 and 1‐methyl‐2‐Ar‐4,6‐diphenyl‐1,2‐dihydro‐ s ‐triazines ( 19a,b ). Triazines 19a and 19b were also prepared by condensation of N ‐methylbenzamidine with benzaldehyde and p ‐tolualdehyde, respectively. Thermolysis of 14d (R = C 6 H 5 , R 1 = CH 2 C 6 H 5 ,Ar = C 6 H 5 ) gave 1‐benzyl‐2,4,6‐triphenyl‐1,2‐dihydro‐ s ‐triazine ( 19c ) and N ‐benzylidenebenzylamine. Mechanistic aspects of these reactions are discussed.

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