Transformation of indoline spiropyrans to bridged 1,3-benzoxazepino[3,2-a]indoles via carbanions stabilized by a cyano group

A. Sackus; E. Valaityte; V. Amankaviciene; Ulf Berg; C. Schichktanz; K. Schlothauer

Transformation of indoline spiropyrans to bridged 1,3-benzoxazepino[3,2-a]indoles via carbanions stabilized by a cyano group

A. Sackus, E. Valaityte, V. Amankaviciene, Ulf Berg, C. Schichktanz, K. Schlothauer

Centre for Analysis and Synthesis

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

Abstract

Condensation of 1-cyanomethyl-2,3,3-trimethyl-3H-indolium perchlorate with ortho-hydroxy-substituted aromatic aldehydes afforded 1-cyanomethylindoline spiropyrans. The latter underwent rearrangement to bridged 1,3-benzoxazepino[3,2-a]indoles on treatment with a base. The mechanism of the rearrangement includes generation of a carbanion stabilized by a cyano Group.

Original language	Russian
Pages (from-to)	1322-1327
Journal	Himiâ Geterocikliceskih Soedinenij
Issue number	9
Publication status	Published - 2007

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

Organic Chemistry

Free keywords

13-methano-1
3-benzoxazepino[3
5a
2-a]indoles. spiropyrans
carbanions
cyclization

Cite this

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title = "Transformation of indoline spiropyrans to bridged 1,3-benzoxazepino[3,2-a]indoles via carbanions stabilized by a cyano group",

abstract = "Condensation of 1-cyanomethyl-2,3,3-trimethyl-3H-indolium perchlorate with ortho-hydroxy-substituted aromatic aldehydes afforded 1-cyanomethylindoline spiropyrans. The latter underwent rearrangement to bridged 1,3-benzoxazepino[3,2-a]indoles on treatment with a base. The mechanism of the rearrangement includes generation of a carbanion stabilized by a cyano Group.",

keywords = "13-methano-1, 3-benzoxazepino[3, 5a, 2-a]indoles. spiropyrans, carbanions, cyclization",

author = "A. Sackus and E. Valaityte and V. Amankaviciene and Ulf Berg and C. Schichktanz and K. Schlothauer",

note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)",

year = "2007",

language = "ryska",

pages = "1322--1327",

journal = "Himi{\^a} Geterocikliceskih Soedinenij",

issn = "0132-6244",

publisher = "Khimiya Geterotsiklicheskikh Soedineniya",

number = "9",

}

TY - JOUR

T1 - Transformation of indoline spiropyrans to bridged 1,3-benzoxazepino[3,2-a]indoles via carbanions stabilized by a cyano group

AU - Sackus, A.

AU - Valaityte, E.

AU - Amankaviciene, V.

AU - Berg, Ulf

AU - Schichktanz, C.

AU - Schlothauer, K.

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

PY - 2007

Y1 - 2007

N2 - Condensation of 1-cyanomethyl-2,3,3-trimethyl-3H-indolium perchlorate with ortho-hydroxy-substituted aromatic aldehydes afforded 1-cyanomethylindoline spiropyrans. The latter underwent rearrangement to bridged 1,3-benzoxazepino[3,2-a]indoles on treatment with a base. The mechanism of the rearrangement includes generation of a carbanion stabilized by a cyano Group.

AB - Condensation of 1-cyanomethyl-2,3,3-trimethyl-3H-indolium perchlorate with ortho-hydroxy-substituted aromatic aldehydes afforded 1-cyanomethylindoline spiropyrans. The latter underwent rearrangement to bridged 1,3-benzoxazepino[3,2-a]indoles on treatment with a base. The mechanism of the rearrangement includes generation of a carbanion stabilized by a cyano Group.

KW - 13-methano-1

KW - 3-benzoxazepino[3

KW - 5a

KW - 2-a]indoles. spiropyrans

KW - carbanions

KW - cyclization

UR - http://dx.doi.org/10.1007/s10593-007-0172-0

M3 - Artikel i vetenskaplig tidskrift

SN - 0132-6244

SP - 1322

EP - 1327

JO - Himiâ Geterocikliceskih Soedinenij

JF - Himiâ Geterocikliceskih Soedinenij

IS - 9

ER -

Transformation of indoline spiropyrans to bridged 1,3-benzoxazepino[3,2-a]indoles via carbanions stabilized by a cyano group

Abstract

Bibliographical note

Subject classification (UKÄ)

Free keywords

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Cite this