1,6-Conjugate addition initiated formal [4+2] annulation of p-quinone methides with sulfonyl allenols: a unique access to spiro[5.5]undeca-1,4-dien-3-one scaffolds

An expedient one-pot synthesis of carbocyclic spiro[5.5]undeca-1,4-dien-3-ones via 1,6-conjugate addition initiated formal [4+2] annulation sequences by employing p-quinone methides and sulfonyl allenols.

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One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides

RSC Advances ◽

10.1039/d0ra05497f ◽

2020 ◽

Vol 10 (55) ◽

pp. 33455-33460

Author(s):

Junwei Wang ◽

Xiang Pan ◽

Quanjin Rong ◽

Lei Zhao ◽

Lin Zhao ◽

...

Keyword(s):

Conjugate Addition ◽

Quinone Methides ◽

One Pot ◽

One Pot Synthesis

A facile one-pot synthesis has been developed through alkylation/acylation of ortho-tosylaminophenyl-substituted para-quinone methides followed by an intramolecular 1,6-conjugate addition and oxidation sequence.

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Tandem Fries Reaction–Conjugate Addition under Microwave Irradiation in Dry Media; One-pot Synthesis of Flavanones

Journal of Chemical Research ◽

10.1177/174751989902300928 ◽

1999 ◽

Vol 23 (9) ◽

pp. 574-575

Author(s):

Firouz Matloubi Moghaddam ◽

Mohammad Ghaffarzadeh ◽

Seyed Hossein Abdi-Oskoui

Keyword(s):

Microwave Irradiation ◽

Silica Gel ◽

Conjugate Addition ◽

Solvent Free ◽

Naphthalene Derivatives ◽

One Pot ◽

Fries Rearrangement ◽

One Pot Synthesis ◽

Solvent Free Conditions ◽

Fries Reaction

An AICl3–ZnCl2 mixture supported on silica gel is found to be an efficient medium for the Fries rearrangement of acyloxybenzene or naphthalene derivatives in solvent-free conditions under microwave irradiation.

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Direct Propargylation of ortho-Quinone Methides with Alkynyl Zinc Reagents: An Application to the One-Pot Synthesis of 2,3-Disubstituted Benzofurans

Synlett ◽

10.1055/s-0039-1691739 ◽

2020 ◽

Vol 31 (08) ◽

pp. 818-822

Author(s):

Hongjun Ren ◽

Manman Sun ◽

Jinyu Song ◽

Lei Wang ◽

Wenguang Yin ◽

...

Keyword(s):

Transition Metal ◽

Functional Group ◽

Quinone Methides ◽

One Pot ◽

Metal Free ◽

Efficient Strategy ◽

One Pot Synthesis ◽

Subsequent Cyclization ◽

The One

A transition-metal-free propargylation of ortho-quinone methides (o-QMs) with alkynyl zinc reagents was achieved. A conjugate alkynylation of an o-QM and subsequent cyclization sequence in the presence of KOt-Bu for the synthesis of 2,3-disubstituted benzofurans in one pot was developed. This efficient strategy exhibits good functional-group compatibility and gives moderate to good yields. The present reaction might serve as an attractive method for the synthesis of polysubstituted benzofurans.

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Conjugate addition of isocyanides to chromone 3-carboxylic acid: an efficient one-pot synthesis of chroman-4-one 2-carboxamides

Organic & Biomolecular Chemistry ◽

10.1039/c2ob07011a ◽

2012 ◽

Vol 10 (17) ◽

pp. 3406 ◽

Cited By ~ 17

Author(s):

Ana G. Neo ◽

Jesús Díaz ◽

Stefano Marcaccini ◽

Carlos F. Marcos

Keyword(s):

Carboxylic Acid ◽

Conjugate Addition ◽

One Pot ◽

One Pot Synthesis

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Metal-Free One-Pot Synthesis of 3-Phosphinoylbenzofurans via Phospha-Michael Addition/Cyclization of H-Phosphine Oxides and in Situ Generated ortho-Quinone Methides

Organic Letters ◽

10.1021/acs.orglett.7b03863 ◽

2018 ◽

Vol 20 (2) ◽

pp. 477-480 ◽

Cited By ~ 34

Author(s):

Ji-Yuan Du ◽

Yan-Hua Ma ◽

Rui-Qing Yuan ◽

Nana Xin ◽

Shao-Zhen Nie ◽

...

Keyword(s):

Michael Addition ◽

Phosphine Oxides ◽

Quinone Methides ◽

One Pot ◽

Metal Free ◽

One Pot Synthesis

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Highly Selective One-Pot Synthesis of Polysubstituted Isoflavanes using Styryl Ethers and Electron-Withdrawing ortho-Quinone Methides Generated In Situ

Synlett ◽

10.1055/s-0037-1611361 ◽

2018 ◽

Vol 30 (02) ◽

pp. 189-192 ◽

Cited By ~ 6

Author(s):

Yujiro Hoshino ◽

Kiyoshi Honda ◽

Kenta Tanaka ◽

Mami Kishimoto ◽

Naoya Ohtsuka ◽

...

Keyword(s):

Biologically Active ◽

Quinone Methides ◽

One Pot ◽

One Pot Synthesis ◽

Reaction Proceeds ◽

Acidic Conditions ◽

High Yields

A highly selective one-pot synthesis of polysubstituted isoflavanes has been developed. The reaction proceeds through the cycloaddition of methyl styryl ethers, derived from phenylacetaldehyde dimethyl acetals under acidic conditions, with electron-withdrawing ortho-quinone methides generated in situ. When phenylacetaldehyde dimethyl acetals were reacted with salicylaldehydes, the reaction proceeded smoothly to afford the corresponding isoflavanes stereoselectively in high yields and with excellent regioselectivities. The present reaction provides versatile access to functionalized isoflavanes, and constitutes a useful tool for the synthesis of biologically active molecules.

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