Methylene Meldrum's Acid Derivatives of Indoxyl and Their Cyclization Reactions under Flash Vacuum Pyrolysis Conditions

Alexander P. Gaywood; Hamish McNab

doi:10.1055/s-0029-1218668

Methylene Meldrum's Acid Derivatives of Indoxyl and Their Cyclization Reactions under Flash Vacuum Pyrolysis Conditions

Alexander P. Gaywood, Hamish McNab

School of Chemistry

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

Abstract

Pure indoxyl can be obtained in 75% yield by flash vacuum pyrolysis (FVP) of 2'-azidoacetophenone at 650 degrees C. Reaction of indoxyl with methoxymethylene Meldrum's acid takes place at the 1-position, and FVP of the resulting derivative provides 1-hydroxy-9H-pyrrolo[1,2-a]indol-9-one (54%). FVP of the isomeric 2methylene compound gives pyrano[3,2-b]indol-2(5H)-one (42%).

Original language	English
Pages (from-to)	1361-1364
Number of pages	4
Journal	Synthesis: Journal of Synthetic Organic Chemistry
Issue number	8
DOIs	https://doi.org/10.1055/s-0029-1218668
Publication status	Published - Apr 2010

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title = "Methylene Meldrum's Acid Derivatives of Indoxyl and Their Cyclization Reactions under Flash Vacuum Pyrolysis Conditions",

abstract = "Pure indoxyl can be obtained in 75% yield by flash vacuum pyrolysis (FVP) of 2'-azidoacetophenone at 650 degrees C. Reaction of indoxyl with methoxymethylene Meldrum's acid takes place at the 1-position, and FVP of the resulting derivative provides 1-hydroxy-9H-pyrrolo[1,2-a]indol-9-one (54%). FVP of the isomeric 2methylene compound gives pyrano[3,2-b]indol-2(5H)-one (42%).",

author = "Gaywood, {Alexander P.} and Hamish McNab",

year = "2010",

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doi = "10.1055/s-0029-1218668",

language = "English",

pages = "1361--1364",

journal = "Synthesis: Journal of Synthetic Organic Chemistry",

issn = "0039-7881",

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T1 - Methylene Meldrum's Acid Derivatives of Indoxyl and Their Cyclization Reactions under Flash Vacuum Pyrolysis Conditions

AU - Gaywood, Alexander P.

AU - McNab, Hamish

PY - 2010/4

Y1 - 2010/4

N2 - Pure indoxyl can be obtained in 75% yield by flash vacuum pyrolysis (FVP) of 2'-azidoacetophenone at 650 degrees C. Reaction of indoxyl with methoxymethylene Meldrum's acid takes place at the 1-position, and FVP of the resulting derivative provides 1-hydroxy-9H-pyrrolo[1,2-a]indol-9-one (54%). FVP of the isomeric 2methylene compound gives pyrano[3,2-b]indol-2(5H)-one (42%).

AB - Pure indoxyl can be obtained in 75% yield by flash vacuum pyrolysis (FVP) of 2'-azidoacetophenone at 650 degrees C. Reaction of indoxyl with methoxymethylene Meldrum's acid takes place at the 1-position, and FVP of the resulting derivative provides 1-hydroxy-9H-pyrrolo[1,2-a]indol-9-one (54%). FVP of the isomeric 2methylene compound gives pyrano[3,2-b]indol-2(5H)-one (42%).

U2 - 10.1055/s-0029-1218668

DO - 10.1055/s-0029-1218668

M3 - Article

SN - 0039-7881

SP - 1361

EP - 1364

JO - Synthesis: Journal of Synthetic Organic Chemistry

JF - Synthesis: Journal of Synthetic Organic Chemistry

IS - 8

ER -

Methylene Meldrum's Acid Derivatives of Indoxyl and Their Cyclization Reactions under Flash Vacuum Pyrolysis Conditions

Abstract

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