Rapid synthesis of 1,3,5-substituted 1,2,4-triazoles from carboxylic acids, amidines, and hydrazines

Journal of Organic Chemistry

Volumn 76, Issue 4, 2011, Pages 1177-1179

  Castanedo, Georgette M ^a   Seng, Pamela S ^a   Blaquiere, Nicole ^a   Trapp, Sean ^a   Staben, Steven T ^a  

^a GENENTECH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GENERAL METHOD; ONE POT PROCESS; RAPID SYNTHESIS; REGIO-SELECTIVE;

CARBOXYLIC ACIDS; HYDRAZINE;

SYNTHESIS (CHEMICAL);

AMIDINE; CARBOXYLIC ACID; HYDRAZINE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; SYNTHESIS;

AMIDINES; CARBOXYLIC ACIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDRAZINES; MOLECULAR STRUCTURE; TRIAZOLES;

EID: 79951633283     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1023393     Document Type: Article

References (17)

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14. In contrast, reaction of 4-propyloxybenzoyl chloride with benzamidine gave a complex mixture of products.
15. a of the conjugate acid of 3 = 7.13.
16. Common byproduct observed by LC-MS include primary amide formation, reaction of HATU with amidine to form guanidinyl by-product, acid/amidine dimer and reaction of hydrazine with carboxylic acid (indicating incomplete formation of acylamidine intermediate). Isolated yields seem highly dependent on the solubility of the triazole products.
17. Notably, all reagents utilized in this publication are commercially available.