Pictet-Spengler reactions of Tryptamine and tryptophan with cycloalkanones and ketonic Mannich bases

E. M. Afsah; M. Hammouda; W. S. Hamama

doi:10.1007/BF00809161

Pictet-Spengler reactions of Tryptamine and tryptophan with cycloalkanones and ketonic Mannich bases

E. M. Afsah
, M. Hammouda
, W. S. Hamama

Mansoura University

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

11 Scopus citations

Abstract

A Pictet-Spengler reaction of Tryptamine (1) with cyclopentanone under physiological conditions gave 3-(cyclopentylideneaminoethyl)indole (3), which was cyclized to the 1-spirocyclic 1,2,3,4-tetrahydro-2-carboline (4). Treatment of (±)-tryptophan with cyclopentanone and cyclohexanone in acidic medium afforded the spirocyclic systems 5 and 6, respectively. The Pictet-Spengler reaction was extended further using ketonic bis-Mannich bases, to give compounds 7 and 8. The possibility of using other types of ketonic bases was investigated.

Original language	English
Pages (from-to)	851-855
Number of pages	5
Journal	Monatshefte fur Chemie
Volume	116
Issue number	6-7
DOIs	https://doi.org/10.1007/BF00809161
State	Published - Jun 1985
Externally published	Yes

Keywords

1-Spirocyclic 1,2,3,4-tetrahydro-2-carbolines

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10.1007/BF00809161

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title = "Pictet-Spengler reactions of Tryptamine and tryptophan with cycloalkanones and ketonic Mannich bases",

abstract = "A Pictet-Spengler reaction of Tryptamine (1) with cyclopentanone under physiological conditions gave 3-(cyclopentylideneaminoethyl)indole (3), which was cyclized to the 1-spirocyclic 1,2,3,4-tetrahydro-2-carboline (4). Treatment of (±)-tryptophan with cyclopentanone and cyclohexanone in acidic medium afforded the spirocyclic systems 5 and 6, respectively. The Pictet-Spengler reaction was extended further using ketonic bis-Mannich bases, to give compounds 7 and 8. The possibility of using other types of ketonic bases was investigated.",

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author = "Afsah, \{E. M.\} and M. Hammouda and Hamama, \{W. S.\}",

year = "1985",

month = jun,

doi = "10.1007/BF00809161",

language = "English",

volume = "116",

pages = "851--855",

journal = "Monatshefte fur Chemie",

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T1 - Pictet-Spengler reactions of Tryptamine and tryptophan with cycloalkanones and ketonic Mannich bases

AU - Afsah, E. M.

AU - Hammouda, M.

AU - Hamama, W. S.

PY - 1985/6

Y1 - 1985/6

N2 - A Pictet-Spengler reaction of Tryptamine (1) with cyclopentanone under physiological conditions gave 3-(cyclopentylideneaminoethyl)indole (3), which was cyclized to the 1-spirocyclic 1,2,3,4-tetrahydro-2-carboline (4). Treatment of (±)-tryptophan with cyclopentanone and cyclohexanone in acidic medium afforded the spirocyclic systems 5 and 6, respectively. The Pictet-Spengler reaction was extended further using ketonic bis-Mannich bases, to give compounds 7 and 8. The possibility of using other types of ketonic bases was investigated.

AB - A Pictet-Spengler reaction of Tryptamine (1) with cyclopentanone under physiological conditions gave 3-(cyclopentylideneaminoethyl)indole (3), which was cyclized to the 1-spirocyclic 1,2,3,4-tetrahydro-2-carboline (4). Treatment of (±)-tryptophan with cyclopentanone and cyclohexanone in acidic medium afforded the spirocyclic systems 5 and 6, respectively. The Pictet-Spengler reaction was extended further using ketonic bis-Mannich bases, to give compounds 7 and 8. The possibility of using other types of ketonic bases was investigated.

KW - 1-Spirocyclic 1,2,3,4-tetrahydro-2-carbolines

UR - https://www.scopus.com/pages/publications/6544281195

U2 - 10.1007/BF00809161

DO - 10.1007/BF00809161

M3 - Article

AN - SCOPUS:6544281195

SN - 0026-9247

VL - 116

SP - 851

EP - 855

JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

IS - 6-7

ER -

Pictet-Spengler reactions of Tryptamine and tryptophan with cycloalkanones and ketonic Mannich bases

Abstract

Keywords

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