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Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction. / Usmanova, Liliia; Bakulina, Olga; Dar’in, Dmitry; Krasavin, Mikhail.

In: Chemistry of Heterocyclic Compounds, Vol. 53, No. 4, 01.04.2017, p. 474-479.

Research output: Contribution to journal › Article › peer-review

Harvard

Usmanova, L, Bakulina, O, Dar’in, D & Krasavin, M 2017, 'Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction', Chemistry of Heterocyclic Compounds, vol. 53, no. 4, pp. 474-479. https://doi.org/10.1007/s10593-017-2076-y

APA

Usmanova, L., Bakulina, O., Dar’in, D., & Krasavin, M. (2017). Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction. Chemistry of Heterocyclic Compounds, 53(4), 474-479. https://doi.org/10.1007/s10593-017-2076-y

Vancouver

Usmanova L, Bakulina O, Dar’in D, Krasavin M. Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction. Chemistry of Heterocyclic Compounds. 2017 Apr 1;53(4):474-479. https://doi.org/10.1007/s10593-017-2076-y

Author

Usmanova, Liliia ; Bakulina, Olga ; Dar’in, Dmitry ; Krasavin, Mikhail. / Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction. In: Chemistry of Heterocyclic Compounds. 2017 ; Vol. 53, No. 4. pp. 474-479.

BibTeX

@article{719e828b09754ce38fcc8fae4a199111,
title = "Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction",
abstract = "[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).",
keywords = "Castagnoli–Cushman reaction, intramolecular SAr reaction, post-MCR modification, tricyclic lactones-lactams",
author = "Liliia Usmanova and Olga Bakulina and Dmitry Dar{\textquoteright}in and Mikhail Krasavin",
year = "2017",
month = apr,
day = "1",
doi = "10.1007/s10593-017-2076-y",
language = "English",
volume = "53",
pages = "474--479",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer Nature",
number = "4",

}

RIS

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 -

ID: 34635132