TBHP-promoted oxidative cyclization of o-alkynylquinoline aldehydes: Metal/additive-free domino synthesis of pyrano[4,3-b]quinolin-1-ones

被引：9

作者：

Singh, Jay Bahadur ^{[1
]}

Mishra, Kalpana ^{[1
]}

Gupta, Tanu ^{[1
]}

Singh, Radhey M. ^{[1
]}

机构：

[1] Banaras Hindu Univ, Inst Sci, Ctr Adv Study, Dept Chem, Varanasi, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 11期

关键词：

Metal free; Additive free; Radical reaction; TBHP; Pyrano[4,3-b]quinolin-1-ones; ONE-POT SYNTHESIS; C-H FUNCTIONALIZATION; TERT-BUTYL PERESTERS; ELECTROPHILIC CYCLIZATION; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; INTRAMOLECULAR CARBONYLATION; PYRANOQUINOLINE ALKALOIDS; QUINOLINE ALKALOIDS; SELECTIVE SYNTHESIS;

D O I：

10.1016/j.tetlet.2018.01.083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

TBHP-promoted domino synthesis of pyrano[4,3-b]quinolin-1-ones is described from o-alkynylquinoline aldehydes. The radical reaction proceeded without metal and additive via oxidation of aldehydic C-H bond into C-OH bond followed by intramolecular 6-endo-dig cyclization. The probable mechanism is discussed. (C) 2018 Published by Elsevier Ltd.

引用

页码：1019 / 1022

页数：4

共 11 条

[1] An economical nucleophilic route toward facile synthesis of pyrano[4,3-b]quinolin-1-ones via 6-endo-dig cyclization of o-alkynylquinoline esters
Sharma, Neha
Asthana, Mrityunjaya
Nandini, Durgesh
Singh, R. P.
Singh, Radhey M.
TETRAHEDRON, 2013, 69 (07) : 1822 - 1829
[2] An efficient ultrasound promoted catalyst-free protocol for the synthesis of chromeno[4,3-b]quinolin-6-ones
Prasad, J. Venkata
Reddy, J. Satyanarayana
Kumar, N. Ravi
Solomon, K. Anand
Gopikrishna, G.
JOURNAL OF CHEMICAL SCIENCES, 2011, 123 (05) : 673 - 679
[3] Base-free NIS promoted electrophilic cyclization of alkynes: an efficient synthesis of iodo substituted pyrano[4,3-b]quinolines
Singh, Bhawana
Chandra, Atish
Singh, Seema
Singh, Radhey M.
TETRAHEDRON, 2011, 67 (02) : 505 - 511
[4] Aerobic, metal-free synthesis of 6H-chromeno[4,3-b]quinolin-6-ones
Ton, Nhan N. H.
Dang, Ha V.
Phan, Nam T. S.
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[5] Design, synthesis and cytotoxicity of pyrano[4,3-b]indol-1(5H)-ones: A hybrid pharmacophore approach via gold catalyzed cyclization
Praveen, Chandrasekar
Ananth, D. Babu
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (10) : 2507 - 2512
[6] Efficient synthesis of pyrano[4,3-b]indol-1(5H)-ones from CO2 and alkynyl indoles promoted by a protic ionic liquid
Li, Chun
Jiang, Jian
Li, Linlin
Zhang, Ling
Chen, Qian
Wang, Mengna
Fu, Changli
Zhang, Lin
TETRAHEDRON LETTERS, 2020, 61 (44)
[7] Synthesis of 1H-pyrano[4,3-b]benzofuran-1-one derivatives via photochemical cyclization of substituted 4H-furo[3,2-c]pyran-4-ones
Milyutin, Constantine, V
Lichitsky, Boris, V
Melekhina, Valeriya G.
Komogortsev, Andrey N.
Fakhrutdinov, Artem N.
Minyaev, Mikhail E.
Krayushkin, Michail M.
TETRAHEDRON LETTERS, 2020, 61 (44)
[8] Ultrasound mediated catalyst free synthesis of 6H-1-benzopyrano [4,3-b]quinolin-6-ones leading to novel quinoline derivatives: Their evaluation as potential anti-cancer agents
Mulakayala, Naveen
Rambabu, D.
Raja, Mohan Rao
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Kalle, Arunasree M.
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Reddy, C. Malla
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[9] TBHP/TBAI-Mediated Oxidative Cascade Reaction Consisting of Dimerization, Cyclization, and 1,2-Aryl Migration: Metal-Free Synthesis of Pyrrolin-4-ones and Highly Substituted Pyrroles
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Zhang, Yong
Deng, Jun
Zhang-Negrerie, Daisy
Du, Yunfei
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23): : 12682 - 12690
[10] A Novel Synthesis of 1-Aryl-6-bromo-3-(5-ethylthio-4-phenyl-4H-1,2,4-triazol-3-yl)-1H-pyrazolo[4,3-b]quinolin-9(4H)-ones via Thermal Cyclization of 4-Azidopyrazoles
Medrasi, Hanadi Y.
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JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (04) : 1159 - 1167

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