Diastereoselective Spirocyclization via Intramolecular C(sp3)-H Bond Functionalization Triggered by Sequential [1,5]-Hydride Shift/Cyclization Process: Approach to Spiro-tetrahydroquinolines

被引：10

作者：

Bhowmik, Arup ^{[1
]}

Das, Sumit ^{[1
,2
]}

Sarkar, Writhabrata ^{[1
]}

Saidalavi, K. M. ^{[1
]}

Mishra, Aniket ^{[1
]}

Roy, Anupama ^{[1
]}

Deb, Indubhusan ^{[1
]}

机构：

[1] Indian Inst Chem Biol, Organ & Med Chem Div, 4 Raja SC Mullick Rd, Kolkata 700032, India

[2] Acad Sci & Innovat Res AcSIR, Kamla Nehru Nagar 201002, Ghaziabad, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 03期

关键词：

1,5]-hydride shift reaction; Lewis acid catalyst; Spirocycles; tetrahydroisoquinoline; 2-coumaranone; 3-isochromanone; C-H BOND; RING-CLOSURE REACTIONS; HYDRIDE TRANSFER; ASYMMETRIC-SYNTHESIS; HETEROCYCLIC SYNTHESIS; CATALYZED DIRECT; TOPOISOMERASE-I; CASCADE; CONSTRUCTION; TANDEM;

D O I：

10.1002/adsc.202001011

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A direct synthesis of spiro[5.5]and [5.4]-tetrahydroquinolines has been developed through C(sp(3))-H bond functionalization triggered by sequential [1,5]- hydride shift /cyclization sequence using ortho amino benzaldehydes and active methylene compounds such as 2-coumaranone, 4-hydroxycoumarin, 3-coumaranone, and 3-isochromanone. This protocol provides a Lewis acid catalyst-free straight forward one-pot reaction in cases of 2-coumaranone and 4-hydroxycoumarin, Lewis acid-catalyzed stepwise reaction for 3-coumaranone and 3-isochromanone to access a wide range of spiro-heterocycles in excellent to good yields and diastereoselectivity.

引用

页码：826 / 832

页数：7

共 112 条

[21] Aminocatalytic Enantioselective 1, 6-Addition of (Nitromethyl)benzenes to α, β, γ, δ-Cyclic Dienones [J].

Feng, Kai-Xiang ;

Shen, Qiao-Yu ;

Zheng, Ya-Yun ;

Xia, Ai-Bao ;

Zhou, Zhan-Yu ;

Tang, Cheng-Ke ;

Zhong, Ai-Guo ;

Xu, Dan-Qian ;

Du, Xiao-Hua .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (39) :6626-6630

[22] Total Syntheses of 7,20-Oxa-Bridged Dinorditerpenes: Antihepatitis C Virus Active (+)-Elevenol from Flueggea virosa and (+)-Przewalskin [J].

Fischer, Michel ;

Harms, Klaus ;

Koert, Ulrich .

ORGANIC LETTERS, 2016, 18 (21) :5692-5695

[23]

Gandamana D. A., 2018, ANGEW CHEM, V130, P6289

[24] New modified eremophilanes from the roots of Psacalium radulifolium [J].

Garduño-Ramírez, ML ;

Trejo, A ;

Navarro, V ;

Bye, R ;

Linares, E ;

Delgado, G .

JOURNAL OF NATURAL PRODUCTS, 2001, 64 (04) :432-435

[25] Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2H)-benzofuranone derivatives [J].

Hadj-esfandiari, Narges ;

Navidpour, Latifeh ;

Shadnia, Hooman ;

Amini, Mohsen ;

Samadi, Nasrm ;

Faramarzi, Mohammad Ali ;

Shafiee, Abbas .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (22) :6354-6363

[26] Redox-Neutral Indole Annulation Cascades [J].

Haibach, Michael C. ;

Deb, Indubhusan ;

De, Chandra Kanta ;

Seidel, Daniel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) :2100-2103

[27] Highly Efficient and Stereoselective Construction of Dispiro-[oxazolidine-2-thione]bisoxindoles and Dispiro [imidazolidine-2-thione]bisoxindoles [J].

Han, Yan-Yan ;

Chen, Wen-Bing ;

Han, Wen-Yong ;

Wu, Zhi-Jun ;

Zhang, Xiao-Mei ;

Yuan, Wei-Cheng .

ORGANIC LETTERS, 2012, 14 (02) :490-493

[28] Synthesis of New Spirocyclopropane and Oxadiazole Products [J].

Haouas, Amel ;

Ben Hamadi, Naoufel ;

Msaddek, Moncef .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) :1765-1768

[29]

Haudecoeur R, 2012, CURR MED CHEM, V19, P2861

[30] Asymmetric sp3 C-H functionalization via a chiral Bronsted acid-catalyzed redox reaction for the synthesis of cyclic aminals [J].

He, Yu-Ping ;

Du, Yu-Liu ;

Luo, Shi-Wei ;

Gong, Liu-Zhu .

TETRAHEDRON LETTERS, 2011, 52 (52) :7064-7066

← 1 2 3 4 5 6 7 8 9 10 →