NOVEL RING ENLARGEMENT OF LACTAMS VIA QUINAZOLINONE ANNELATION - A FACILE ROUTE TO BENZOANNELATED LARGE-MEMBERED CYCLIC 1,5-DIAMINES

被引：41

作者：

TAKEUCHI, H ^{[1
]}

MATSUSHITA, Y ^{[1
]}

EGUCHI, S ^{[1
]}

机构：

[1] NAGOYA UNIV,FAC ENGN,INST APPL ORGAN CHEM,FURO CHO,CHIKUSA KU,NAGOYA 46401,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 04期

关键词：

D O I：

10.1021/jo00004a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel route to benzoannelated large-membered cyclic 1,5-diamines from lactams is described. Thus, n-membered lactams 1 were N-acylated by o-azidobenzoyl chloride 5 to afford the corresponding imides 4. These were treated with tributylphosphine and underwent an intramolecular aza-Wittig reaction to give n-membered ring-fused quinazolinones 2 in 84-96% yield. By reductive cleavage of 2 with BH3.THF, (n+4)-membered cyclic diamines 3 were obtained in 52-95% yield.

引用

页码：1535 / 1537

页数：3

共 19 条

[1] 1H-INDAZOLE AND 2H-INDAZOLE BY THERMAL AND PHOTOLYTIC DECOMPOSITION OF ORTHO-AZIDOBENZOIC ACID AND ORTHO-AZIDOBENZALDEHYDE DERIVATIVES [J].

ARDAKANI, MA ;

SMALLEY, RK ;

SMITH, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2501-2506

[2] THE REACTIVITY OF IMIDE CARBONYL GROUPS IN THE INTRAMOLECULAR AZA-WITTIG REACTION - AN EFFICIENT ROUTE TO IMINOLACTAM DERIVATIVES [J].

EGUCHI, S ;

TAKEUCHI, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (09) :602-603

[3]

ISAACS NS, 1987, PHYSICAL ORGANIC CHE, P287

[4] APPLICATION OF THE INTRAMOLECULAR AZA-WITTIG REACTION TO THE SYNTHESIS OF VINYLOGOUS URETHANES AND AMIDES [J].

LAMBERT, PH ;

VAULTIER, M ;

CARRIE, R .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5352-5356

[5] A NEW EFFICIENT ACCESS TO CYCLIC IMINES [J].

LAMBERT, PH ;

VAULTIER, M ;

CARRIE, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (21) :1224-1225

[6] INTRAMOLECULAR TRAPPING OF A PHOSPHAZIDE BY AN IMINE - FORMATION OF 2,3-DIAMINO-2H-INDAZOLE DERIVATIVES FROM ORTHO-AZIDOBENZALDIMINES AND TERTIARY PHOSPHINES [J].

MOLINA, P ;

ARQUES, A ;

VINADER, MV .

TETRAHEDRON LETTERS, 1989, 30 (45) :6237-6240

[7] NEW METHODOLOGY FOR THE PREPARATION OF QUINAZOLINE DERIVATIVES VIA TANDEM AZA-WITTIG/HETEROCUMULENE-MEDIATED ANNULATION - SYNTHESIS OF 4(3H)-QUINAZOLINONES, BENZIMIDAZO[1,2-C]QUINAZOLINES, QUINAZOLINO[3,2-A]QUINAZOLINES AND BENZOTHIAZOLO[3,2-C]QUINAZOLINES [J].

MOLINA, P ;

ALAJARIN, M ;

VIDAL, A ;

FOCESFOCES, MD ;

CANO, FH .

TETRAHEDRON, 1989, 45 (13) :4263-4286

[8]

PELTER A, 1988, BORON REAGENTS, P128

[9]

SANDHU JS, 1975, CHEM IND-LONDON, P569

[10] NOVEL SYNTHESIS AND REACTIVITY OF 4-AZAHOMOADAMANT-3-ENE AND 4-AZA-4-HOMOBREND-3-ENES VIA INTRAMOLECULAR AZA-WITTIG REACTIONS [J].

SASAKI, T ;

EGUCHI, S ;

OKANO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5912-5913

← 1 2 →