Cyclization of 2-azidobenzophenones to 3-phenylanthranils. Examples of an intramolecular 1, 3-dipolar addition

JH Hall, FE Behr, RL Reed

Index: Hall,J.H. et al. Journal of the American Chemical Society, 1972 , vol. 94, p. 4952 - 4958

Full Text: HTML

Citation Number: 42

Abstract

Abstract: The rate of decomposition of 4'-substituted-2-azidobenzophenones to give 4'- substituted-3-phenyl-anthranils has been studied in decalin over a 45'temperature range. The reaction was found to be accelerated by electron-withdrawing groups and retarded by electron-donating groups. The enthalpy of activation was found to be considerably less than reported for phenyl azide decompositions. The entropy of activation was moderately large ...

Related Articles:

Synthesis of 2-aminobenzophenones via rapid halogen-lithium exchange in the presence of a 2-amino-N-methoxy-N-methylbenzamide

[Frye, Stephen V.; Johnson, Marty C.; Valvano, Nicole L. Journal of Organic Chemistry, 1991 , vol. 56, # 11 p. 3750 - 3752]

Synthesis of a new generation reverse transcriptase inhibitor via the BCl 3/GaCl 3-induced condensation of anilines with nitriles (sugasawa reaction)

[Houpis, Ioannis N.; Molina, Audrey; Douglas, Alan W.; Xavier, Lyndon; Lynch, Joseph; et al. Tetrahedron Letters, 1994 , vol. 35, # 37 p. 6811 - 6814]

A one-pot process for palladium catalyzed direct C–H acylation of anilines in water using a removable ortho directing group

[Szabo, Fruzsina; Simko, Daniel; Novak, Zoltan RSC Advances, 2014 , vol. 4, # 8 p. 3883 - 3886]

Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: a new series of selective COX-2 inhibitors

[Hu, Wenhui; Guo, Zongru; Chu, Fengming; Bai, Aiping; Yi, Xiang; Cheng, Guifang; Li, Jing Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 7 p. 1153 - 1160]

Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: a new series of selective COX-2 inhibitors

[Hu, Wenhui; Guo, Zongru; Chu, Fengming; Bai, Aiping; Yi, Xiang; Cheng, Guifang; Li, Jing Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 7 p. 1153 - 1160]

More Articles...