TY - JOUR

T1 - Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction

AU - Usmanova, Liliia

AU - Bakulina, Olga

AU - Dar’in, Dmitry

AU - Krasavin, Mikhail

PY - 2017/4/1

Y1 - 2017/4/1

N2 - [Figure not available: see fulltext.] Castagnoli–Cushman reaction of imines derived from 2-chloropyridine-3-carboxaldehyde with a cyclic anhydride (4-(methylsulfonyl)-morpholine-2,6-dione) conducted at 110°C in DMF over 1 h, as expected, led to a mixture of trans- and cis-configured carboxylic acids. However, the latter underwent a spontaneous intramolecular reaction of the carboxylic functionality onto the labile nearby 2-chloropyridine moiety to give the respective tricyclic lactones in 17–23% yield, along with 41–68% yield of the uncyclized trans-configured products (isolated as methyl esters).

AB - [Figure not available: see fulltext.] Castagnoli–Cushman reaction of imines derived from 2-chloropyridine-3-carboxaldehyde with a cyclic anhydride (4-(methylsulfonyl)-morpholine-2,6-dione) conducted at 110°C in DMF over 1 h, as expected, led to a mixture of trans- and cis-configured carboxylic acids. However, the latter underwent a spontaneous intramolecular reaction of the carboxylic functionality onto the labile nearby 2-chloropyridine moiety to give the respective tricyclic lactones in 17–23% yield, along with 41–68% yield of the uncyclized trans-configured products (isolated as methyl esters).

KW - Castagnoli–Cushman reaction

KW - intramolecular SAr reaction

KW - post-MCR modification

KW - tricyclic lactones-lactams

UR - http://www.scopus.com/inward/record.url?scp=85019211004&partnerID=8YFLogxK

U2 - 10.1007/s10593-017-2076-y

DO - 10.1007/s10593-017-2076-y

M3 - Article

AN - SCOPUS:85019211004

VL - 53

SP - 474

EP - 479

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 4

ER -