Access to 2,3-Fused Pyrroles via Visible Light Driven Coupling of α-Azidochalcones with 1/2-Naphthols, or 2-Hydroxy-1,4-Naphthoquinone

被引：38

作者：

Borra, Satheesh ^{[1
,2
]}

Chandrasekhar, D. ^{[1
,2
]}

Newar, Uma Devi ^{[1
]}

Maurya, Ram Awatar ^{[1
,2
]}

机构：

[1] NEIST, CSIR, Chem Sci & Technol Div, Appl Organ Chem Grp, Jorhat 785006, Assam, India

[2] NEIST, CSIR, Acad Sci & Innovat Res AcSIR, Jorhat 785006, Assam, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 02期

关键词：

ONE-POT SYNTHESIS; VINYL AZIDES; PHOTOREDOX CATALYSIS; CHEMICAL-SYNTHESIS; FUNCTIONALIZATION; DERIVATIVES; PRECURSORS;

D O I：

10.1021/acs.joc.8b02459

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Azidochalcones were coupled with 1/2-naphthols or 2-hydroxy-1,4-naphthoquinone using Ru(bpy)(3)(PF6)(2) as a photocatalyst under blue LED light irradiation to yield 2,3-fused pyrroles in high yields (68-84%). The overall transformation involves photosensitized decomposition of alpha-azidochalcones into highly reactive 2H-azirines which are trapped by 1/2-naphthols or 2-hydroxy-1,4-naphthoquinone, leading to the construction of two new C-N and one new C-C bonds.

引用

页码：1042 / 1052

页数：11

共 59 条

[1] Visible Light Mediated Aryl Migration by Homolytic C-N Cleavage of Aryl Amines [J].

Alpers, Dirk ;

Cole, Kevin P. ;

Stephenson, Corey R. J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (37) :12167-12170

[2] Reactions of methyl 2-aryl-2H-azirine-3-carboxylates with nucleophiles [J].

Alves, MJ ;

Gilchrist, TL ;

Sousa, JH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (10) :1305-1310

[3] Tricyanomethane and Its Ketenimine Tautomer: Generation from Different Precursors and Analysis in Solution, Argon Matrix, and as a Single Crystal [J].

Banert, Klaus ;

Chityala, Madhu ;

Hagedorn, Manfred ;

Beckers, Helmut ;

Stueker, Tony ;

Riedel, Sebastian ;

Rueffer, Tobias ;

Lang, Heinrich .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (32) :9582-9586

[4] A NEW SYNTHESIS OF PYRROLES FROM NITROALKENES [J].

BARTON, DHR ;

ZARD, SZ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1098-1100

[5] A telescoped protocol for the synthesis of new pyrrolo [3,4-d]pyridazinones by cascade reactions [J].

Bonacorso, Helio G. ;

Libero, Francieli M. ;

Dal Forno, Gean M. ;

Pittaluga, Everton P. ;

Porte, Liliane M. F. ;

Martins, Marcos A. P. ;

Zanatta, Nilo .

TETRAHEDRON LETTERS, 2015, 56 (37) :5190-5195

[6] Access to 1a,6b-Dihydro-1H-benzofuro[2,3-b]azirines and Benzofuran-2-amines via Visible Light Triggered Decomposition of α-Azidochalcones [J].

Borra, Satheesh ;

Chandrasekhar, D. ;

Khound, Susmita ;

Maurya, Ram Awatar .

ORGANIC LETTERS, 2017, 19 (19) :5364-5367

[7] Visible-Light Driven Photocascade Catalysis: Union of N,N-Dimethylanilines and α-Azidochalcones in Flow Microreactors [J].

Borra, Satheesh ;

Chandrasekhar, D. ;

Adhikary, Susanta ;

Rasala, Sandeep ;

Gokulnath, Sabapathi ;

Maurya, Ram Awatar .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (04) :2249-2256

[8] Engaging sulfinate salts via Ni/photoredox dual catalysis enables facile Csp2-SO2R coupling [J].

Cabrera-Afonso, Maria Jesus ;

Lu, Zhi-Peng ;

Kelly, Christopher B. ;

Lang, Simon B. ;

Dykstra, Ryan ;

Gutierrez, Osvaldo ;

Molander, Gary A. .

CHEMICAL SCIENCE, 2018, 9 (12) :3186-3191

[9] Visible Light Driven Photocascade Catalysis: Ru(bpy)3(PF6)2/TBHP-Mediated Synthesis of Fused β-Carbolines in Batch and Flow Microreactors [J].

Chandrasekhar, D. ;

Borra, Satheesh ;

Nanubolu, Jagadeesh Babu ;

Maurya, Ram Awatar .

ORGANIC LETTERS, 2016, 18 (12) :2974-2977

[10] Synthesis of polysubstituted N-H pyrroles from vinyl azides and 1,3-dicarbonyl compounds [J].

Chiba, Shunsuke ;

Wang, Yi-Feng ;

Lapointe, Guillaume ;

Narasaka, Koichi .

ORGANIC LETTERS, 2008, 10 (02) :313-316

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