Synthesis of Perinaphthenones via BF3.Et2O Mediated One-Pot Cascade 4,5-Annulation Reactions of 1-Naphthols and Ynones

Chun Wei Kuo; Naidu Sambasiva Rao; Prakash Bhimrao Patil; Ting Ta Chiang; Veerababurao Kavala; Ching Fa Yao

doi:10.1002/adsc.202001558

Synthesis of Perinaphthenones via BF₃^.Et₂O Mediated One-Pot Cascade 4,5-Annulation Reactions of 1-Naphthols and Ynones

Chun Wei Kuo
, Naidu Sambasiva Rao
, Prakash Bhimrao Patil
, Ting Ta Chiang
, Veerababurao Kavala
, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

5 Citations (Scopus)

Abstract

C₄-C₅ periannulation of 1-naphthols and ynones via BF₃^.Et₂O mediated one-pot cascade under metal and solvent-free conditions have been developed for the synthesis of perinaphthenones. Furthermore, this strategy features the formation of new periannulation at C₄-C₅ positions of α-naphthol, synthesis of highly substituted perinaphthenones, broad substrate scope, readily available starting materials and good to moderate yields. The perinaphthenones products synthesized here have exhibited interesting photo physical properties. (Figure presented.).

Original language	English
Pages (from-to)	1935-1943
Number of pages	9
Journal	Advanced Synthesis and Catalysis
Volume	363
Issue number	7
DOIs	https://doi.org/10.1002/adsc.202001558
Publication status	Published - 2021 Mar 29

Keywords

Periannulation
Perinaphthenones
Solvent-Free
Ynones
α-naphthol

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.202001558

Cite this

@article{e02d99dbb703471caa2e3287213ce74e,

title = "Synthesis of Perinaphthenones via BF3.Et2O Mediated One-Pot Cascade 4,5-Annulation Reactions of 1-Naphthols and Ynones",

abstract = "C4-C5 periannulation of 1-naphthols and ynones via BF3.Et2O mediated one-pot cascade under metal and solvent-free conditions have been developed for the synthesis of perinaphthenones. Furthermore, this strategy features the formation of new periannulation at C4-C5 positions of α-naphthol, synthesis of highly substituted perinaphthenones, broad substrate scope, readily available starting materials and good to moderate yields. The perinaphthenones products synthesized here have exhibited interesting photo physical properties. (Figure presented.).",

keywords = "Periannulation, Perinaphthenones, Solvent-Free, Ynones, α-naphthol",

author = "Kuo, \{Chun Wei\} and Rao, \{Naidu Sambasiva\} and Patil, \{Prakash Bhimrao\} and Chiang, \{Ting Ta\} and Veerababurao Kavala and Yao, \{Ching Fa\}",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = mar,

day = "29",

doi = "10.1002/adsc.202001558",

language = "English",

volume = "363",

pages = "1935--1943",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "7",

}

TY - JOUR

T1 - Synthesis of Perinaphthenones via BF3.Et2O Mediated One-Pot Cascade 4,5-Annulation Reactions of 1-Naphthols and Ynones

AU - Kuo, Chun Wei

AU - Rao, Naidu Sambasiva

AU - Patil, Prakash Bhimrao

AU - Chiang, Ting Ta

AU - Kavala, Veerababurao

AU - Yao, Ching Fa

PY - 2021/3/29

Y1 - 2021/3/29

N2 - C4-C5 periannulation of 1-naphthols and ynones via BF3.Et2O mediated one-pot cascade under metal and solvent-free conditions have been developed for the synthesis of perinaphthenones. Furthermore, this strategy features the formation of new periannulation at C4-C5 positions of α-naphthol, synthesis of highly substituted perinaphthenones, broad substrate scope, readily available starting materials and good to moderate yields. The perinaphthenones products synthesized here have exhibited interesting photo physical properties. (Figure presented.).

AB - C4-C5 periannulation of 1-naphthols and ynones via BF3.Et2O mediated one-pot cascade under metal and solvent-free conditions have been developed for the synthesis of perinaphthenones. Furthermore, this strategy features the formation of new periannulation at C4-C5 positions of α-naphthol, synthesis of highly substituted perinaphthenones, broad substrate scope, readily available starting materials and good to moderate yields. The perinaphthenones products synthesized here have exhibited interesting photo physical properties. (Figure presented.).

KW - Periannulation

KW - Perinaphthenones

KW - Solvent-Free

KW - Ynones

KW - α-naphthol

UR - https://www.scopus.com/pages/publications/85100907559

UR - https://www.scopus.com/pages/publications/85100907559#tab=citedBy

U2 - 10.1002/adsc.202001558

DO - 10.1002/adsc.202001558

M3 - Article

AN - SCOPUS:85100907559

SN - 1615-4150

VL - 363

SP - 1935

EP - 1943

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 7

ER -

Synthesis of Perinaphthenones via BF₃^.Et₂O Mediated One-Pot Cascade 4,5-Annulation Reactions of 1-Naphthols and Ynones

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 2031304: Experimental Crystal Structure Determination

CCDC 2031303: Experimental Crystal Structure Determination

CCDC 2031305: Experimental Crystal Structure Determination

Cite this

Synthesis of Perinaphthenones via BF3.Et2O Mediated One-Pot Cascade 4,5-Annulation Reactions of 1-Naphthols and Ynones

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 2031304: Experimental Crystal Structure Determination

CCDC 2031303: Experimental Crystal Structure Determination

CCDC 2031305: Experimental Crystal Structure Determination

Cite this

Synthesis of Perinaphthenones via BF₃^.Et₂O Mediated One-Pot Cascade 4,5-Annulation Reactions of 1-Naphthols and Ynones