Synthesis of S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides and specificities of their base-catalyzed intramolecular heterocyclizations into naphtho[1,2,3-cd]-indol-6(2H)-ones

Synthesis of S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides and specificities of their base-catalyzed intramolecular heterocyclizations into naphtho[1,2,3-cd]-indol-6(2H)-ones Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2013, Volume: 49, Number: 1, Pages: 70-77 Pages count : 8 DOI: 10.1134/S1070428013010132

Authors

Kargina O.I. ¹ , Gornostaev L.M. ¹ , Nefedov A.A. ²

Affiliations

1	(Данные Web of science) Astafev Krasnoyarsk State Pedag Univ, Krasnoyarsk 660049, Russia
2	(Данные Web of science) Russian Acad Sci, Siberian Branch, Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

Heating of 6H-anthra[1,9-cd][1,2]oxazol-6-ones with dialkyl sulfoxides in sulfolane gave S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides which underwent cyclization to naphtho-[1,2,3-cd]indol-6(2H)-one derivatives on heating in boiling tetrahydrofuran in the presence of sodium methoxide. p-Toluenesulfinic acid was isolated as by-product in the cyclization of S-methyl-S-(4-methylphenyl)-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximide. The heterocyclizations of S,S-dipropyl- and S,S-dibutyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides to 1-ethyl- and 1-propylnaphtho[1,2,3-cd]-indol-6(2H)-ones were accompanied by formation of the corresponding 1-[1-hydroxyethyl(propyl)]naphtho-[1,2,3-cd]indol-6(2H)-ones. DOI: 10.1134/S1070428013010132

Kargina O.I. , Gornostaev L.M. , Nefedov A.A.
Synthesis of S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides and specificities of their base-catalyzed intramolecular heterocyclizations into naphtho[1,2,3-cd]-indol-6(2H)-ones
Russian Journal of Organic Chemistry. 2013. V.49. N1. P.70-77. DOI: 10.1134/S1070428013010132 WOS Scopus РИНЦ

Каргина О.И. , Горностаев Л.М. , Нефедов А.А.
Синтез и особенности внутримолекулярных основнокатализируемых гетероциклизаций 1-s,s-диалкил-n-(9,10-антрахинон-1-ил)сульфоксимидов в нафто[1,2,3- cd]индол-6(2 h)-оны
Журнал органической химии (RUSS J ORG CHEM+). 2013. Т.49. №1. С.79-85. РИНЦ

Published print:	Jan 1, 2013
Published online:	Feb 8, 2013

Web of science	WOS:000314696400013
Scopus	2-s2.0-84873643183
Elibrary	20433223
OpenAlex	W2136526176