Aziridination of alkenes with 3-acetoxyaminoquinazolinones in the presence of hexamethyldisilazane

被引：20

作者：

Atkinson, RS ^{[1
]}

Barker, E ^{[1
]}

Ulukanli, S ^{[1
]}

机构：

[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 03期

关键词：

D O I：

10.1039/a704917j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Yields of aziridines from reaction of some alkenes, including alpha,beta-unsaturated esters, with 3-acetoxyamino-2-isopropylquinazolinone 6 (Q(3)NHOAc) are greatly increased in the presence of hexamethyldisilazane (HMDS). A mono-aziridination product of naphthalene is obtained only in the presence of HMDS. It is concluded that the enhanced yields in these aziridinations are the result of scavenging of acetic acid by HMDS, thus prolonging the lifetime of the aziridinating agent Q(3)NHOAc.

引用

页码：583 / 589

页数：7

共 11 条

[1] 3-acetoxyaminoquinazolin-4(3H)-ones as aziridinating agents: Relative rate of inversion at the exocyclic nitrogen
Atkinson, RS
Williams, PJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (02): : 205 - 211
[2] CHIRAL AZIRIDINATION OF ALPHA,BETA-UNSATURATED ESTERS AND KETONES USING N-NITRENES IN THE PRESENCE OF TRIFLUOROACETIC-ACID
ATKINSON, RS
TUGHAN, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12): : 2803 - 2807
[3] AZIRIDINATION OF ALKENES USING 3-AMINO-2-ETHYLQUINAZOLIN-4(3H)-ONE AND LEAD-TETRAACETATE TRIFLUOROACETIC-ACID
ATKINSON, RS
KELLY, BJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (09): : 1627 - 1630
[4] REACTIONS OF CYCLIC BETA-KETO-ESTERS AND OTHER ENOL DERIVATIVES WITH 3-ACETOXYAMINO-2-ISOPROPYLQUINAZOLIN-4(3H)-ONE - FURTHER OXIDATION OF THE CYCLIC ALPHA-(3,4-DIHYDRO-2-ISOPROPYL-4-OXOQUINAZOLIN-3-YL)AMINO KETONES WITH LEAD-TETRAACETATE LEADING TO RING-EXPANSION (IN DICHLOROMETHANE) AND RING-CLEAVAGE (IN METHANOL)
ATKINSON, RS
BARKER, E
EDWARDS, PJ
THOMSON, GA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (12): : 1533 - 1542
[5] AZIRIDINATION OF ALKENES USING 3-ACETOXYAMINOQUINAZOLIN-4-(3H)ONES IN THE PRESENCE OF TERTIARY-AMINES - EVIDENCE FOR AN AZAIMIDE (N-NITRENE) INTERMEDIATE
ATKINSON, RS
BARKER, E
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (08) : 819 - 820
[6] AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES - EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES
ATKINSON, RS
GRIMSHIRE, MJ
KELLY, BJ
[J]. TETRAHEDRON, 1989, 45 (10) : 2875 - 2886
[7] Aziridination of alkenes using 3-acetoxyamino-2-trifluoromethylquinazolin-4(3H)-one
Atkinson, RS
Coogan, MP
Cornell, CL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (02): : 157 - 166
[8] N-(3,4-DIHYDRO-4-OXOQUINAZOLIN-3-YL)PYRIDINIUM IMIDES - AZIRIDINATING AGENTS FOR ALKENES - MEASUREMENT OF ROTATIONAL BARRIERS AROUND EACH N-N BOND IN AN N-N-N SYSTEM
ATKINSON, RS
BARKER, E
EDWARDS, PJ
THOMSON, GA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (07) : 727 - 728
[9] ATKINSON RS, 1997, J CHEM SOC P1, P879
[10] Sheldrick GM., 1993, SHELXL 93 PROGRAM CR, DOI DOI 10.1107/S2053229614026540

← 1 2 →