A simple method for the synthesis of isoindoline derivatives

A simple method for the synthesis of isoindoline derivatives Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 1573-8353 , E-ISSN: 0009-3122

Output data

Year: 2023, Volume: 59, Number: 1-2, Pages: 54-62 Pages count : 9 DOI: 10.1007/s10593-023-03162-6

Authors

Shorokhov Vitaly V. ¹ , Lebedev Danila S. ¹ , Boichenko Maksim A. ¹ , Zhokhov Sergey S. ¹ , Trushkov Igor V. ² , Ivanova Olga A. ¹

Affiliations

1	Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

A method for the synthesis of isoindoline derivatives was developed based on a domino reaction involving a donor-acceptor cyclopropane containing a bromomethyl group in the ortho position of the aromatic substituent and structurally varied primary amines (anilines, benzylamines, cycloalkylamines). It was shown that the resulting N-benzyl-1,3-dihydroisoindole under hydrogenolysis conditions at room temperature underwent selective cleavage of the exocyclic N–CH2Ar bond followed by in situ lactamization to form benzo[b]pyrrolizidinone. The same product was obtained in a domino reaction starting with reduction of the azidomethyl group at the ortho position of the donor aromatic substituent. Similarly, the generation of the o-2-aminoethyl group was accompanied by two successive cyclization reactions leading to the formation of benzo[e]indolizidinone.

Shorokhov V.V. , Lebedev D.S. , Boichenko M.A. , Zhokhov S.S. , Trushkov I.V. , Ivanova O.A.
A simple method for the synthesis of isoindoline derivatives
Chemistry of Heterocyclic Compounds. 2023. V.59. N1-2. P.54-62. DOI: 10.1007/s10593-023-03162-6 WOS Scopus OpenAlex

Web of science:	WOS:000952878800001
Scopus:	2-s2.0-85153855236
OpenAlex:	W4360979522

DB	Citing
OpenAlex	7
Scopus	5
Web of science	4