Facile Synthesis of 2H-Benzo[h]Chromenes via an Arylamine-Catalyzed Mannich Cyclization Cascade Reaction

被引：1

作者：

Zhang, Yueteng ^{[1
,2
,3
,4
]}

Ji, Peng ^{[1
,2
,3
]}

Meng, Xiang ^{[1
,2
,3
]}

Gao, Feng ^{[1
,2
,3
]}

Zeng, Fanxun ^{[1
,2
,3
]}

Wang, Wei ^{[1
,2
,3
]}

机构：

[1] Univ Arizona, Dept Pharmacol & Toxicol, Tucson, AZ 85721 USA

[2] Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA

[3] Univ Arizona, BIO5 Inst, Tucson, AZ 85721 USA

[4] Zhengzhou Univ, Acad Med Sci, Sch Basic Med Sci, 100 Kexue Ave, Zhengzhou 450001, Peoples R China

来源：

MOLECULES | 2021年 / 26卷 / 12期

基金：

中国国家自然科学基金;

关键词：

aminocatalysis; cascade reaction; chromenes; organocatalysis; quinone methide; ONE-POT SYNTHESIS; QUINONE METHIDE; ALPHA; BETA-UNSATURATED ALDEHYDES; NAPHTHOPYRANS; LAPACHENOLE; CHROMANES;

D O I：

10.3390/molecules26123617

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes. The notable feature of the process included the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1- and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.

引用

页数：12

共 34 条

[1] The Domestication of ortho-Quinone Methides
Bai, Wen-Ju
David, Jonathan G.
Feng, Zhen-Gao
Weaver, Marisa G.
Wu, Kun-Liang
Pettus, Thomas R. R.
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) : 3655 - 3664
[2] Stereoselectivity, regioselectivity and mechanism in the intramolecular 'citran' bicyclisation of chromenes
Calderon-Higginson, C
Crombie, L
Redshaw, SD
Whiting, DA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15): : 2491 - 2494
[3] 6,6-DIPHENYL-6H-NAPHTHO(2',3'-2,3)PYRAN AND 4,6-DIPHENYL-4H-NAPHTHO(2',3'-2,3)PYRAN
COTTAM, J
LIVINGST.R
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1965, (NOV): : 6646 - &
[4] Photochromic compounds: Chemistry and application in ophthalmic lenses
Crano, JC
Flood, T
Knowles, D
Kumar, A
VanGemert, B
[J]. PURE AND APPLIED CHEMISTRY, 1996, 68 (07) : 1395 - 1398
[5] Photochromic, thermochromic, and fluorescent spirooxazines and naphthopyrans: A spectrokinetic and thermodynamic study
di Nunzio, Maria R.
Gentili, Pier L.
Romani, Aldo
Favaro, Gianna
[J]. CHEMPHYSCHEM, 2008, 9 (05) : 768 - 775
[6] Solvent-free synthesis of naphthopyrans under ball-milling conditions
Dong, Ya-Wei
Wang, Guan-Wu
Wang, Lei
[J]. TETRAHEDRON, 2008, 64 (44) : 10148 - 10154
[7] Syntheses of Chromenes and Chromanes via o-Quinone Methide Intermediates
Ferreira, Sabrina B.
da Silva, Fernando de C.
Pinto, Angelo C.
Gonzaga, Daniel T. G.
Ferreira, Vitor F.
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (06) : 1080 - 1097
[8] The synthesis and electronic absorption spectra of 3-phenyl-3(4-pyrrolidino-2-substituted phenyl)-3H-naphtho[2,1-b]pyrans:: further exploration of the ortho substituent effect
Gabbutt, CD
Heron, BM
Instone, AC
[J]. TETRAHEDRON, 2006, 62 (04) : 737 - 745
[9] Organocatalytic Asymmetric Friedel-Crafts Alkylation/Cyclization Cascade Reaction of 1-Naphthols and α,β-Unsaturated Aldehydes: An Enantioselective Synthesis of Chromanes and Dihydrobenzopyranes
Hong, Liang
Wang, Lei
Sun, Wangsheng
Wong, Kwokyin
Wang, Rui
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17) : 6881 - 6884
[10] Convenient synthesis of naphthopyrans using montmorillonite K-10 as heterogeneous catalyst
Hosseinzadeh, Rahman
Mohadjerani, Maryam
Ardestanian, Mohammad Javad
Naimi-Jamal, Mohammad Reza
Lasemi, Zahra
[J]. JOURNAL OF CHEMICAL SCIENCES, 2014, 126 (04) : 1081 - 1089

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