HIV REVERSE-TRANSCRIPTASE INHIBITORS - A CONCISE ENE REACTION-BASED SYNTHESIS OF THE 7,8-DIHYDRO-6H,12H-AZEPINO [2,1-B]QUINAZOLINE SYSTEM, AND ITS REACTION WITH NITRILE OXIDES

C  GOULAOUIC-DUBOIS; D R  ADAMS; A  CHIARONI; C  RICHE; F W  FOWLER; D S  GRIERSON

HIV REVERSE-TRANSCRIPTASE INHIBITORS - A CONCISE ENE REACTION-BASED SYNTHESIS OF THE 7,8-DIHYDRO-6H,12H-AZEPINO [2,1-B]QUINAZOLINE SYSTEM, AND ITS REACTION WITH NITRILE OXIDES

C GOULAOUIC-DUBOIS, D R ADAMS, A CHIARONI, C RICHE, F W FOWLER, D S GRIERSON

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

Abstract

The reaction of amide (5), obtained in two steps from 2-amino benzophenone (4) with triflic anhydride, followed by treatment of the in situ generated imodyl triflate (7) with LiCN led to exclusive formation of the tetrahydroquinazoline (10). Thermolysis of this intermediate promoted an ene reaction leading to the azepino-quinazoline (11) (63% yield). The 1,3-dipolar cycloaddition between this product and nitrile oxide (12) proved chemoselective, producing the novel pentacyclic oxadiazine (14) as a 7:3 mixture of diastereomers in 79% yield.

Original language	English
Pages (from-to)	509-512
Number of pages	4
Journal	Heterocycles
Volume	39
Issue number	2
Publication status	Published - 31 Dec 1994

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title = "HIV REVERSE-TRANSCRIPTASE INHIBITORS - A CONCISE ENE REACTION-BASED SYNTHESIS OF THE 7,8-DIHYDRO-6H,12H-AZEPINO [2,1-B]QUINAZOLINE SYSTEM, AND ITS REACTION WITH NITRILE OXIDES",

abstract = "The reaction of amide (5), obtained in two steps from 2-amino benzophenone (4) with triflic anhydride, followed by treatment of the in situ generated imodyl triflate (7) with LiCN led to exclusive formation of the tetrahydroquinazoline (10). Thermolysis of this intermediate promoted an ene reaction leading to the azepino-quinazoline (11) (63% yield). The 1,3-dipolar cycloaddition between this product and nitrile oxide (12) proved chemoselective, producing the novel pentacyclic oxadiazine (14) as a 7:3 mixture of diastereomers in 79% yield.",

author = "C GOULAOUIC-DUBOIS and ADAMS, {D R} and A CHIARONI and C RICHE and FOWLER, {F W} and GRIERSON, {D S}",

year = "1994",

month = dec,

day = "31",

language = "English",

volume = "39",

pages = "509--512",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "2",

}

TY - JOUR

T1 - HIV REVERSE-TRANSCRIPTASE INHIBITORS - A CONCISE ENE REACTION-BASED SYNTHESIS OF THE 7,8-DIHYDRO-6H,12H-AZEPINO [2,1-B]QUINAZOLINE SYSTEM, AND ITS REACTION WITH NITRILE OXIDES

AU - GOULAOUIC-DUBOIS, C

AU - ADAMS, D R

AU - CHIARONI, A

AU - RICHE, C

AU - FOWLER, F W

AU - GRIERSON, D S

PY - 1994/12/31

Y1 - 1994/12/31

N2 - The reaction of amide (5), obtained in two steps from 2-amino benzophenone (4) with triflic anhydride, followed by treatment of the in situ generated imodyl triflate (7) with LiCN led to exclusive formation of the tetrahydroquinazoline (10). Thermolysis of this intermediate promoted an ene reaction leading to the azepino-quinazoline (11) (63% yield). The 1,3-dipolar cycloaddition between this product and nitrile oxide (12) proved chemoselective, producing the novel pentacyclic oxadiazine (14) as a 7:3 mixture of diastereomers in 79% yield.

AB - The reaction of amide (5), obtained in two steps from 2-amino benzophenone (4) with triflic anhydride, followed by treatment of the in situ generated imodyl triflate (7) with LiCN led to exclusive formation of the tetrahydroquinazoline (10). Thermolysis of this intermediate promoted an ene reaction leading to the azepino-quinazoline (11) (63% yield). The 1,3-dipolar cycloaddition between this product and nitrile oxide (12) proved chemoselective, producing the novel pentacyclic oxadiazine (14) as a 7:3 mixture of diastereomers in 79% yield.

M3 - Article

SN - 0385-5414

VL - 39

SP - 509

EP - 512

JO - Heterocycles

JF - Heterocycles

IS - 2

ER -

HIV REVERSE-TRANSCRIPTASE INHIBITORS - A CONCISE ENE REACTION-BASED SYNTHESIS OF THE 7,8-DIHYDRO-6H,12H-AZEPINO [2,1-B]QUINAZOLINE SYSTEM, AND ITS REACTION WITH NITRILE OXIDES

Abstract

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