New Cyclization Mode of [ N ‐(Diarylmethyleneamino)carbonimidoyl]ketenes: Synthesis of 9 H ‐Pyrazolo[3,2‐ b ][1,3]benzoxazines | Zendy

Lisowskaya Natalia A. | Zendy; Alajarin Mateo | Zendy; SanchezAndrada Pilar | Zendy

Premium

New Cyclization Mode of [ N ‐(Diarylmethyleneamino)carbonimidoyl]ketenes: Synthesis of 9 H ‐Pyrazolo[3,2‐ b ][1,3]benzoxazines

Author(s) -

Lisowskaya Natalia A.,

Alajarin Mateo,

SanchezAndrada Pilar

Publication year - 2006

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500768

Subject(s) - decarbonylation , chemistry , pyrrole , ab initio , stereochemistry , medicinal chemistry , reaction mechanism , catalysis , organic chemistry

The thermal decarbonylation of methyl 3‐acyl‐1‐[ o ‐bromophenyl(phenyl)methyleneamino]‐4,5‐dioxo‐4,5‐dihydro‐1 H ‐pyrrole‐2‐carboxylates 2a and 2b gave the novel methyl 3‐acyl‐9‐hydroxy‐9‐phenyl‐9 H ‐pyrazolo[3,2‐ b ][1,3]benzoxazine‐2‐carboxylates 4a and 4b , the structures of which were determined by X‐ray crystallography. The proposed mechanism for this conversion, involving the [ N ‐( o ‐bromo‐α‐phenylbenzylideneamino)carbonimidoyl]ketenes 5 and the mesomeric betaines 6 as intermediates, has been investigated by ab initio and DFT calculations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research