A greener synthesis of 1,8-dioxo-octahydroxanthene derivatives under ultrasound

Naveen Mulakayala; G. Pavan Kumar; D. Rambabu; Madhu Aeluri; M. V. Basaveswara Rao; Manojit Pal

doi:10.1016/j.tetlet.2012.10.024

A greener synthesis of 1,8-dioxo-octahydroxanthene derivatives under ultrasound

Naveen Mulakayala, G. Pavan Kumar, D. Rambabu, Madhu Aeluri, M. V. Basaveswara Rao, Manojit Pal

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

45 Scopus citations

Abstract

The ceric ammonium nitrate (CAN) has been identified as an efficient and eco-friendly catalyst for the one pot and virtually three-component reaction of 5,5-dimethyl-1,3-cyclohexanedione with various aldehydes in 2-propanol. Under ultrasound irradiation, the reaction proceeded smoothly at a faster rate at 50 °C affording a variety of 9-alkyl/aryl/heteroaryl substituted 3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-diones in good to excellent yields. A probable mechanism for this CAN-mediated synthesis of 1,8-dioxo-octahydroxanthene derivatives is presented. Overall, the methodology provides advantages such as low cost, high yields of products and simple operational procedures and is free from the use of harmful chlorinated solvents.

Original language	English
Pages (from-to)	6923-6926
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2012.10.024
State	Published - 19 Dec 2012
Externally published	Yes

Keywords

1,8-Dioxo-octahydroxanthene
Ceric ammonium nitrate (CAN)
One pot synthesis
Ultrasound

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2012.10.024

Cite this

@article{0e5832d8c1b14ab1a0e581e56ad78ab6,

title = "A greener synthesis of 1,8-dioxo-octahydroxanthene derivatives under ultrasound",

abstract = "The ceric ammonium nitrate (CAN) has been identified as an efficient and eco-friendly catalyst for the one pot and virtually three-component reaction of 5,5-dimethyl-1,3-cyclohexanedione with various aldehydes in 2-propanol. Under ultrasound irradiation, the reaction proceeded smoothly at a faster rate at 50 °C affording a variety of 9-alkyl/aryl/heteroaryl substituted 3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-diones in good to excellent yields. A probable mechanism for this CAN-mediated synthesis of 1,8-dioxo-octahydroxanthene derivatives is presented. Overall, the methodology provides advantages such as low cost, high yields of products and simple operational procedures and is free from the use of harmful chlorinated solvents.",

keywords = "1,8-Dioxo-octahydroxanthene, Ceric ammonium nitrate (CAN), One pot synthesis, Ultrasound",

author = "Naveen Mulakayala and {Pavan Kumar}, G. and D. Rambabu and Madhu Aeluri and {Basaveswara Rao}, {M. V.} and Manojit Pal",

year = "2012",

month = dec,

day = "19",

doi = "10.1016/j.tetlet.2012.10.024",

language = "English",

volume = "53",

pages = "6923--6926",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "51",

}

TY - JOUR

T1 - A greener synthesis of 1,8-dioxo-octahydroxanthene derivatives under ultrasound

AU - Mulakayala, Naveen

AU - Pavan Kumar, G.

AU - Rambabu, D.

AU - Aeluri, Madhu

AU - Basaveswara Rao, M. V.

AU - Pal, Manojit

PY - 2012/12/19

Y1 - 2012/12/19

N2 - The ceric ammonium nitrate (CAN) has been identified as an efficient and eco-friendly catalyst for the one pot and virtually three-component reaction of 5,5-dimethyl-1,3-cyclohexanedione with various aldehydes in 2-propanol. Under ultrasound irradiation, the reaction proceeded smoothly at a faster rate at 50 °C affording a variety of 9-alkyl/aryl/heteroaryl substituted 3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-diones in good to excellent yields. A probable mechanism for this CAN-mediated synthesis of 1,8-dioxo-octahydroxanthene derivatives is presented. Overall, the methodology provides advantages such as low cost, high yields of products and simple operational procedures and is free from the use of harmful chlorinated solvents.

AB - The ceric ammonium nitrate (CAN) has been identified as an efficient and eco-friendly catalyst for the one pot and virtually three-component reaction of 5,5-dimethyl-1,3-cyclohexanedione with various aldehydes in 2-propanol. Under ultrasound irradiation, the reaction proceeded smoothly at a faster rate at 50 °C affording a variety of 9-alkyl/aryl/heteroaryl substituted 3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-diones in good to excellent yields. A probable mechanism for this CAN-mediated synthesis of 1,8-dioxo-octahydroxanthene derivatives is presented. Overall, the methodology provides advantages such as low cost, high yields of products and simple operational procedures and is free from the use of harmful chlorinated solvents.

KW - 1,8-Dioxo-octahydroxanthene

KW - Ceric ammonium nitrate (CAN)

KW - One pot synthesis

KW - Ultrasound

UR - http://www.scopus.com/inward/record.url?scp=84869204289&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2012.10.024

DO - 10.1016/j.tetlet.2012.10.024

M3 - Article

AN - SCOPUS:84869204289

SN - 0040-4039

VL - 53

SP - 6923

EP - 6926

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

A greener synthesis of 1,8-dioxo-octahydroxanthene derivatives under ultrasound

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this