Retro-Mannich reactions of 3-alkyl-3,4-dihydro-2H-1,3-benz e oxazines and the synthesis of axially chiral resorcinarenes

Philip C. Bulman Page; Harry Heaney; Matthew J. McGrath; Edward P. Sampler; Robert F. Wilkins

doi:10.1016/s0040-4039(03)00393-9

Retro-Mannich reactions of 3-alkyl-3,4-dihydro-2H-1,3-benz e oxazines and the synthesis of axially chiral resorcinarenes

Philip C. Bulman Page
, Harry Heaney
, Matthew J. McGrath
, Edward P. Sampler
, Robert F. Wilkins

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

21 Citations (Scopus)

Abstract

Intermediates involved in the conversion of 3-alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines into 2-N,N-dialkylaminomethylphenol derivatives, using morpholine and other high boiling secondary amines, have been identified and characterised. Additional experiments have established the involvement of o-quinone methide intermediates in the retro-Mannich reactions. Axially chiral resorcinarenes have been prepared by utilising the exchange reactions. (C) 2003 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	2965-2970
Number of pages	6
Journal	Tetrahedron Letters
Volume	44
Issue number	14
DOIs	https://doi.org/10.1016/s0040-4039(03)00393-9
Publication status	Published - 31 Mar 2003

Keywords

SOLVENT
resorcinarenes
GENERATION
DERIVATIVES
O-QUINONE METHIDE
axially chiral
heterocycles
o-quinone methides
REACTIVITY
aminol ethers

Access to Document

10.1016/s0040-4039(03)00393-9

Cite this

@article{15214ad1b4ee4f94bcf9776cd19ee707,

title = "Retro-Mannich reactions of 3-alkyl-3,4-dihydro-2H-1,3-benz e oxazines and the synthesis of axially chiral resorcinarenes",

abstract = "Intermediates involved in the conversion of 3-alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines into 2-N,N-dialkylaminomethylphenol derivatives, using morpholine and other high boiling secondary amines, have been identified and characterised. Additional experiments have established the involvement of o-quinone methide intermediates in the retro-Mannich reactions. Axially chiral resorcinarenes have been prepared by utilising the exchange reactions. (C) 2003 Elsevier Science Ltd. All rights reserved.",

keywords = "SOLVENT, resorcinarenes, GENERATION, DERIVATIVES, O-QUINONE METHIDE, axially chiral, heterocycles, o-quinone methides, REACTIVITY, aminol ethers",

author = "\{Bulman Page\}, \{Philip C.\} and Harry Heaney and McGrath, \{Matthew J.\} and Sampler, \{Edward P.\} and Wilkins, \{Robert F.\}",

year = "2003",

month = mar,

day = "31",

doi = "10.1016/s0040-4039(03)00393-9",

language = "English",

volume = "44",

pages = "2965--2970",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "14",

}

TY - JOUR

T1 - Retro-Mannich reactions of 3-alkyl-3,4-dihydro-2H-1,3-benz e oxazines and the synthesis of axially chiral resorcinarenes

AU - Bulman Page, Philip C.

AU - Heaney, Harry

AU - McGrath, Matthew J.

AU - Sampler, Edward P.

AU - Wilkins, Robert F.

PY - 2003/3/31

Y1 - 2003/3/31

N2 - Intermediates involved in the conversion of 3-alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines into 2-N,N-dialkylaminomethylphenol derivatives, using morpholine and other high boiling secondary amines, have been identified and characterised. Additional experiments have established the involvement of o-quinone methide intermediates in the retro-Mannich reactions. Axially chiral resorcinarenes have been prepared by utilising the exchange reactions. (C) 2003 Elsevier Science Ltd. All rights reserved.

AB - Intermediates involved in the conversion of 3-alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines into 2-N,N-dialkylaminomethylphenol derivatives, using morpholine and other high boiling secondary amines, have been identified and characterised. Additional experiments have established the involvement of o-quinone methide intermediates in the retro-Mannich reactions. Axially chiral resorcinarenes have been prepared by utilising the exchange reactions. (C) 2003 Elsevier Science Ltd. All rights reserved.

KW - SOLVENT

KW - resorcinarenes

KW - GENERATION

KW - DERIVATIVES

KW - O-QUINONE METHIDE

KW - axially chiral

KW - heterocycles

KW - o-quinone methides

KW - REACTIVITY

KW - aminol ethers

U2 - 10.1016/s0040-4039(03)00393-9

DO - 10.1016/s0040-4039(03)00393-9

M3 - Article

SN - 0040-4039

VL - 44

SP - 2965

EP - 2970

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -