Solid-phase synthesis of 3,4-dihydroquinazoline

被引：53

作者：

Wang, FJ

Hauske, JR

机构：

[1] Dept. of Drug Discov., Sepracor Inc., Marlborough, MA 01752

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(97)10377-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, facile and efficient method for the synthesis of aryl iminophosphorane has been developed by treating a series of Ar-NH2 (1) attached to a solid support with Ph3P and diethyl azodicarboxylate at room temperature. The resulting solid-supported cinnamyl iminophosphorane (4) was treated with an aryl isocyanate to generate the corresponding solid-supported carbodiimide (5), which upon exposure to a secondary amine underwent 1,2-addition followed by an intramolecular Michael addition to afford the desired 3,4-dihydroquinazoline (7). (C) 1997 Elsevier Science Ltd.

引用

页码：8651 / 8654

页数：4

共 22 条

[11] Solid-phase organic reactions .2. A review of the literature Nov 95 Nov 96.
Hermkens, PHH
Ottenheijm, HCJ
Rees, DC
[J]. TETRAHEDRON, 1997, 53 (16) : 5643 - 5678
[12] Hughes D.L., 1992, ORG REACT, V42, P335, DOI [10.1002/0471264180.OR042.02, DOI 10.1002/0471264180.OR042.02]
[13] ISHIKAWA F, 1980, CHEM PHARM BULL, V28, P1357
[14] Multiple simultaneous synthesis of phenolic libraries
Meyers, HV
Dilley, GJ
Durgin, TL
Powers, TS
Winssinger, NA
Zhu, H
Pavia, MR
[J]. MOLECULAR DIVERSITY, 1995, 1 (01) : 13 - 20
[15] MOLINA P, 1994, SYNTHESIS-STUTTGART, P1197
[16] The current status of heterocyclic combinatorial libraries
Nefzi, A
Ostresh, JM
Houghten, RA
[J]. CHEMICAL REVIEWS, 1997, 97 (02) : 449 - 472
[17] CONJUGATED HETEROCUMULENES - SYNTHESIS OF C=C-CONJUGATED CARBODIIMIDES BY A WITTIG-TYPE REACTION OF IMINOPHOSPHORANES WITH ISOCYANATES AND THEIR CYCLOADDITIONS
SAITO, T
NAKANE, M
ENDO, M
YAMASHITA, H
OYAMADA, Y
MOTOKI, S
[J]. CHEMISTRY LETTERS, 1986, (02) : 135 - 138
[18] A facile and efficient carbodiimide-mediated synthesis of dihydroquinazolines via a tandem nucleophilic addition-intramolecular hetero conjugate addition annulation strategy
Saito, T
Tsuda, K
Saito, Y
[J]. TETRAHEDRON LETTERS, 1996, 37 (02) : 209 - 212
[19] STAUDINGER M, 1919, HELV CHIM ACTA, V49, P815
[20] COMBINATORIAL SYNTHESIS - THE DESIGN OF COMPOUND LIBRARIES AND THEIR APPLICATION TO DRUG DISCOVERY
TERRETT, NK
GARDNER, M
GORDON, DW
KOBYLECKI, RJ
STEELE, J
[J]. TETRAHEDRON, 1995, 51 (30) : 8135 - 8173

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