Synthesis of delta-Carbolines and the Alkaloid Quindoline through a Molybdenum-Catalyzed Cadogan Cyclization and their Photoluminescent Properties

Synthesis of delta-Carbolines and the Alkaloid Quindoline through a Molybdenum-Catalyzed Cadogan Cyclization and their Photoluminescent Properties Full article

Journal

Synlett
ISSN: 0936-5214 , E-ISSN: 1437-2096

Output data

Year: 2019, Volume: 30, Number: 8, Pages: 919-923 Pages count : DOI: 10.1055/s-0037-1612416

Tags

quindoline; carbolines; Cadogan cyclization; nitro compounds; acylpyruvates; cyclic hydroxymethylene ketones

Authors

Shuvalov Vladislav Yu. ^1,2 , Rupp Anna S. ¹ , Kuratova Anna K. ¹ , Fisyuk Alexander S. ^1,2 , Nefedov Andrey A. ³ , Sagitullina Galina P. ¹

Affiliations

1	(Данные Web of science) FM Dostoevsky Omsk State Univ, Dept Organ Chem, 55a Mira Ave, Omsk 644077, Russia
2	(Данные Web of science) Omsk State Tech Univ, Lab New Organ Mat, 11 Mira Ave, Omsk 644050, Russia
3	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Inst Organ Chem, Siberian Branch, 9 Lavrentiev Ave, Novosibirsk 630090, Russia

Cadogan reductive cyclization of substituted 2-aryl-3-nitropyridines to give. -carbolines was performed under MoO2Cl2(DMF) 2 catalysis with triphenylphosphine as a ligand. A new approach for the synthesis of the alkaloid quindoline based on a Mo(VI)-catalyzed Cadogan reductive cyclization of 2-phenyl-3-nitro-5,6,7,8-tetrahydroquinoline followed by aromatization of the resulting 2,3,4,10-tetrahydro-1H-indolo[ 3,2-b] quinoline is proposed. Various.-nitroarylpyridines, obtained by reacting acylpyruvates and cyclic hydroxymethylene ketones with nitroacetophenone enamines, were used as starting compounds for the preparation of. -carbolines. The synthesized. -carbolines were found to act as phosphors; their photophysical properties were studied and a structure-property relationship was revealed.

Shuvalov V.Y. , Rupp A.S. , Kuratova A.K. , Fisyuk A.S. , Nefedov A.A. , Sagitullina G.P.
Synthesis of delta-Carbolines and the Alkaloid Quindoline through a Molybdenum-Catalyzed Cadogan Cyclization and their Photoluminescent Properties
Synlett. 2019. V.30. N8. P.919-923. DOI: 10.1055/s-0037-1612416 WOS Scopus РИНЦ

Published online:	Apr 10, 2019
Published print:	May 1, 2019

Web of science	WOS:000467271100007
Scopus	2-s2.0-85065157330
Elibrary	38672012
OpenAlex	W2936319468