Ring-opening reactions of N-aryl-1,2,3,4-tetrahydroisoquinolines: Synthesis of novel isoquino[2,1-a][3,1]benzoxazine derivatives

Stephen Stanforth

doi:10.1016/S0040-4020(99)01015-7

Ring-opening reactions of N-aryl-1,2,3,4-tetrahydroisoquinolines: Synthesis of novel isoquino[2,1-a][3,1]benzoxazine derivatives

Stephen Stanforth

Applied Sciences Department

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

6 Citations (Scopus)

Abstract

The aldehydes 7e and 7h were prepared by treatment of the 1,2,3,4- tetrahydroisoquinolines 5e and 5h, respectively, with N-bromosuccinimide (NBS). Basic hydrolysis of compounds 7e and 7h gave the 4bH,6H-isoquino[2,1- a][3,1]benzoxazine derivatives 9 (R=H, OMe). Heterocycle 10 was obtained from the reaction of compound 5c with NBS and isolated as the ethyl derivative 11.

Original language	English
Pages (from-to)	461-464
Journal	Tetrahedron
Volume	56
Issue number	3
DOIs	https://doi.org/10.1016/S0040-4020(99)01015-7
Publication status	Published - 14 Jan 2000

Keywords

Isoquino[2
1-a][3
1]benzoxazines
ring-opening
Tetrahydroisoquinolines

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10.1016/S0040-4020(99)01015-7

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title = "Ring-opening reactions of N-aryl-1,2,3,4-tetrahydroisoquinolines: Synthesis of novel isoquino[2,1-a][3,1]benzoxazine derivatives",

abstract = "The aldehydes 7e and 7h were prepared by treatment of the 1,2,3,4- tetrahydroisoquinolines 5e and 5h, respectively, with N-bromosuccinimide (NBS). Basic hydrolysis of compounds 7e and 7h gave the 4bH,6H-isoquino[2,1- a][3,1]benzoxazine derivatives 9 (R=H, OMe). Heterocycle 10 was obtained from the reaction of compound 5c with NBS and isolated as the ethyl derivative 11.",

keywords = "Isoquino[2, 1-a][3, 1]benzoxazines, ring-opening, Tetrahydroisoquinolines",

author = "Stephen Stanforth",

year = "2000",

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day = "14",

doi = "10.1016/S0040-4020(99)01015-7",

language = "English",

volume = "56",

pages = "461--464",

journal = "Tetrahedron",

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TY - JOUR

T1 - Ring-opening reactions of N-aryl-1,2,3,4-tetrahydroisoquinolines: Synthesis of novel isoquino[2,1-a][3,1]benzoxazine derivatives

AU - Stanforth, Stephen

PY - 2000/1/14

Y1 - 2000/1/14

N2 - The aldehydes 7e and 7h were prepared by treatment of the 1,2,3,4- tetrahydroisoquinolines 5e and 5h, respectively, with N-bromosuccinimide (NBS). Basic hydrolysis of compounds 7e and 7h gave the 4bH,6H-isoquino[2,1- a][3,1]benzoxazine derivatives 9 (R=H, OMe). Heterocycle 10 was obtained from the reaction of compound 5c with NBS and isolated as the ethyl derivative 11.

AB - The aldehydes 7e and 7h were prepared by treatment of the 1,2,3,4- tetrahydroisoquinolines 5e and 5h, respectively, with N-bromosuccinimide (NBS). Basic hydrolysis of compounds 7e and 7h gave the 4bH,6H-isoquino[2,1- a][3,1]benzoxazine derivatives 9 (R=H, OMe). Heterocycle 10 was obtained from the reaction of compound 5c with NBS and isolated as the ethyl derivative 11.

KW - Isoquino[2

KW - 1-a][3

KW - 1]benzoxazines

KW - ring-opening

KW - Tetrahydroisoquinolines

U2 - 10.1016/S0040-4020(99)01015-7

DO - 10.1016/S0040-4020(99)01015-7

M3 - Article

SN - 0040-4020

VL - 56

SP - 461

EP - 464

JO - Tetrahedron

JF - Tetrahedron

IS - 3

ER -

Ring-opening reactions of N-aryl-1,2,3,4-tetrahydroisoquinolines: Synthesis of novel isoquino[2,1-a][3,1]benzoxazine derivatives

Abstract

Keywords

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