Synthesis of Luminescent Indolo[2,1-b]quinazolin-6(12H)-ones via a Sequential Ugi/Iodine-Promoted Cyclization/Staudinger/Aza-Wittig Reaction

被引：7

作者：

Yang, Mao-Lin ^{[1
]}

Zhao, Long ^{[1
]}

Chen, Hao-Ran ^{[1
]}

Ding, Ming-Wu ^{[1
]}

机构：

[1] Cent China Normal Univ, Natl Key Lab Green Pesticide, Hubei Int Sci & Technol Cooperat Base Pesticide &, Wuhan 430079, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 23期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; TRYPTANTHRINS; CYCLIZATION; PHARMACOPHORE; CASCADE; ISATINS; DYES; UGI;

D O I：

10.1021/acs.joc.3c01955

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient synthesis of indolo-[2,1-b]-quinazolin-6-(12H)-ones via a sequential Ugi/iodine-promoted cyclization/Staudinger/aza-Wittig reaction was developed. The acid catalyzed three-component reactions of 2-azidobenzaldehydes, 2-[2-(trimethylsilyl)-ethynyl]-benzenamines (or o-aminoacetophenones), and isocyanides gave Ugi-3CR intermediates, which reacted subsequently with I-2/DMSO and triphenylphosphine to produce indolo-[2,1-b]-quinazolin-6-(12H)-ones in good overall yields. The obtained indolo-[2,1-b]-quinazolin-6-(12H)-ones were all colored in bright red or orange. Their luminescent property was studied preliminarily and some of them showed high molar absorption coefficients, strong fluorescence emission intensity, and good absolute light quantum yields.

引用

页码：16424 / 16434

页数：11

共 37 条

[21] Facile synthesis of 11-aryl-6H-isoindolo[2,1-a]-indol-6-ones via hypervalent iodine(III)-promoted cascade cyclization
Dev, Kapil
Maurya, Rakesh
RSC ADVANCES, 2015, 5 (17) : 13102 - 13106
[22] EFFICIENT SYNTHESIS AND BIOLOGICAL PROPERTIES OF 6-ARYL-10-CHLORO-8-IODO-12H-[1,8] NAPHTHYRIDINO [2,1-b] QUINAZOLIN-12-ONES
Mogilaiah, K.
Rao, P. Koteswara
Rao, A. Nageswara
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 25 (02) : 101 - 104
[23] ECO-FRIENDLY SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 6-ARYL-10-NITRO-12H-[1,8] NAPHTHYRIDINO [2,1-b] QUINAZOLIN-12-ONES
Mogilaiah, K.
Prasad, D. Hari
Rao, P. Koteswara
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 23 (04) : 393 - 398
[24] Synthesis of Indolo[2,1-a]isoquinolin-6(5H)-Ones Derivatives via Fe(OTf)3-Promoted Tandem Selenylation/Cyclization of 2-Arylindoles
Zhang, Jia-Rong
Liu, Hao-Yang
Fan, Tao
Chen, Yan-Yan
Xu, Yan-Li
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) : 497 - 504
[25] Facile synthesis of 5H-benzo[b] carbazol-6-yl ketones via sequential reaction of Cu-catalyzed Friedel-Crafts alkylation, iodine-promoted cyclization, nucleophilic substitution and aromatization
Wu, Jing
Wang, Dongping
Wang, Haolong
Wu, Fan
Li, Xincheng
Wan, Boshun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (35) : 6806 - 6811
[26] 1-Butyl-2-methylpipyridinium iodide ([BMPPY]I): novel ionic liquid for the synthesis of 6-hydroxy-6-(1H-indol-3-yl)indolo[2,1-b]quinazolin-12(6H)-ones under green solvent-free conditions
Kobra Nikoofar
Seyedeh Shima Peyrovebaghi
Research on Chemical Intermediates, 2019, 45 : 4287 - 4298
[27] 1-Butyl-2-methylpipyridinium iodide ([BMPPY]I): novel ionic liquid for the synthesis of 6-hydroxy-6-(1H-indol-3-yl)indolo[2,1-b]quinazolin-12(6H)-ones under green solvent-free conditions
Nikoofar, Kobra
Peyrovebaghi, Seyedeh Shima
RESEARCH ON CHEMICAL INTERMEDIATES, 2019, 45 (09) : 4287 - 4298
[28] Synthesis and properties of 6,6-di(indol-3-yl)-indolo[2,1-b]quinazolin-12(6H)-one and its 2,8-dimethyl and 2,8-dibromo derivatives
T. V. Moskovkina
A. I. Kalinovskii
E. A. Martyyas
M. M. Anisimov
Chemistry of Heterocyclic Compounds, 2013, 49 : 452 - 456
[29] Synthesis and properties of 6,6-di(indol-3-yl)-indolo[2,1-b]quinazolin-12(6H)-one and its 2,8-dimethyl and 2,8-dibromo derivatives
Moskovkina, T. V.
Kalinovskii, A. I.
Martyyas, E. A.
Anisimov, M. M.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (03) : 452 - 456
[30] Efficient Synthesis of 2-Substituted Quinolino[7′, 8′:5, 6]pyrano-[2, 3-d]pyrimidin-4(3H)-ones via Tandem Aza-Wittig Reaction
Fang Zheng-dong
Wang Guo-hong
Wang Dun-jia
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2009, 25 (06) : 866 - 869

← 1 2 3 4 →