Abstract
α-Bromoacylpolymethylbenzenes 2a-m react with fuming nitric acid in acetic anhydride to give 2-(nitromethyl)-(α-bromoacyl)polymethylbenzenes 3a-m in good isolated yields. Compounds 3a-j undergo the intramolecular nucleophilic substitution/cyclization in the presence of 1 equiv. of base either in benzene or N,N-dimethylformamide (DMF) to provide the corresponding substituted 3-nitroindan-1-ones 4a-j in quantitative yields as mixtures of diastereomers ( cis and trans). The cis/trans ratios of 4 vary with the steric factor and the nature of solvent: cis < trans in benzene, whereas cis > trans in DMF. On the contrary, 3-unsubstituted 2-nitromethyl compounds 3k-m afford 3,2-benzoxazepin-5(4 H)-ones 7k-m under the same reaction condition. On the other hand, the reactions of 3a-j in the presence of 2 equiv. of base give the substituted inden-1-ones 5 in satisfactory isolated yields.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
