Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence

Raju Adepu; Jadhav Rahul Dhanaji; Polasani Samatha; Prathama S. Mainkar; Srivari Chandrasekhar

doi:10.1021/acs.orglett.0c02749

Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence

Raju Adepu, Jadhav Rahul Dhanaji, Polasani Samatha, Prathama S. Mainkar, Srivari Chandrasekhar

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.

Original language	English
Pages (from-to)	8224-8228
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.0c02749
State	Published - 6 Nov 2020
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.0c02749

Cite this

@article{b49c8d9a69d747ccb30984a56ae355f1,

title = "Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence",

abstract = "A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.",

author = "Raju Adepu and Dhanaji, {Jadhav Rahul} and Polasani Samatha and Mainkar, {Prathama S.} and Srivari Chandrasekhar",

note = "Funding Information: The authors thank the Council of Scientific and Industrial Research (CSIR), Ministry of Science and Technology, Govt. of India. R.A. thanks the Department of Science & Technology (DST) New Delhi for an Inspire Faculty fellowship and grant (DST/INSPIRE/04/2018/001635). J.R.D. thanks CSIR for a research fellowship. S.C. thanks the Science and Engineering Research Board (SERB), Government of India for the J C Bose fellowship (SB/S2/JCB-002/2015) and (VI-D8P/513/2014-15/TDT(G)). We gratefully acknowledge Dr. Balasubramanian Sridhar, Laboratory of X-ray Crystallography, CSIR-IICT, for X-ray analysis. CSIR-IICT manuscript number IICT/Pubs./2020/229. Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = nov,

day = "6",

doi = "10.1021/acs.orglett.0c02749",

language = "English",

volume = "22",

pages = "8224--8228",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence

AU - Adepu, Raju

AU - Dhanaji, Jadhav Rahul

AU - Samatha, Polasani

AU - Mainkar, Prathama S.

AU - Chandrasekhar, Srivari

N1 - Funding Information: The authors thank the Council of Scientific and Industrial Research (CSIR), Ministry of Science and Technology, Govt. of India. R.A. thanks the Department of Science & Technology (DST) New Delhi for an Inspire Faculty fellowship and grant (DST/INSPIRE/04/2018/001635). J.R.D. thanks CSIR for a research fellowship. S.C. thanks the Science and Engineering Research Board (SERB), Government of India for the J C Bose fellowship (SB/S2/JCB-002/2015) and (VI-D8P/513/2014-15/TDT(G)). We gratefully acknowledge Dr. Balasubramanian Sridhar, Laboratory of X-ray Crystallography, CSIR-IICT, for X-ray analysis. CSIR-IICT manuscript number IICT/Pubs./2020/229. Publisher Copyright: © 2020 American Chemical Society.

PY - 2020/11/6

Y1 - 2020/11/6

N2 - A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.

AB - A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.

UR - http://www.scopus.com/inward/record.url?scp=85095862322&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c02749

DO - 10.1021/acs.orglett.0c02749

M3 - Article

C2 - 33081468

AN - SCOPUS:85095862322

SN - 1523-7060

VL - 22

SP - 8224

EP - 8228

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this