One-Pot Three-Component Synthesis of 3,4-Dihydroquinazoline Derivatives

doi:10.6023/cjoc202204059

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3740-3746.DOI: 10.6023/cjoc202204059 Previous Articles Next Articles

Original article

三组分一锅法合成3,4-二氢喹唑啉衍生物

赵龙, 阳茂林, 陈皓冉, 丁明武^*()

华中师范大学农药与化学生物学教育部重点实验室武汉 430079

收稿日期:2022-04-25 修回日期:2022-06-28 发布日期:2022-07-20
通讯作者: 丁明武
基金资助:
国家自然科学基金(21572075)

One-Pot Three-Component Synthesis of 3,4-Dihydroquinazoline Derivatives

Long Zhao, Maolin Yang, Haoran Chen, Mingwu Ding()

Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079

Received:2022-04-25 Revised:2022-06-28 Published:2022-07-20
Contact: Mingwu Ding
Supported by:
National Natural Science Foundation of China(21572075)

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Abstract

A new one-pot synthesis of 3,4-dihydroquinazolines by diethyl azodicarboxylate (DEAD)-promoted oxidative Ugi/ aza-Wittig reaction was developed. The reactions of iminophosphoranes 5, N-aryl-1,2,3,4-tetrahydroisoquinolines 6 and acids 7 produced 3-(tetrahydroisoquinolin-1-formyl) substituted 3,4-dihydroquinazolines 8 in moderate to good yields in the presence of DEAD by tandem oxidative Ugi/aza-Wittig reaction.

Key words: 3,4-dihydroquinazoline-one, iminophosphorane, isocyanide, oxidative Ugi reaction, aza-Wittig reaction

Cite this article

Long Zhao, Maolin Yang, Haoran Chen, Mingwu Ding. One-Pot Three-Component Synthesis of 3,4-Dihydroquinazoline Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3740-3746.

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Fig. & Tab. 6

References 24

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Product	R¹	Ar	R²	Yield^a/%
8a	H	Ph	Ph	75
8b	H	Ph	4-CH₃C₆H₄	73
8c	H	Ph	4-ClC₆H₄	72
8d	H	4-BrC₆H₄	2-BrC₆H₄	63
8e	H	4-BrC₆H₄	4-CH₃OC₆H₄	64
8f	H	4-BrC₆H₄	CH₃	80
8g	H	4-BrC₆H₄	Bu	69
8h	H	4-BrC₆H₄	i-Pr	49
8i	H	4-CH₃C₆H₄	Thiophen-2-yl	80
8j	H	4-CH₃C₆H₄	Cyclohexyl	56
8k	4-CH₃	Ph	Ph	74
8l	5-Cl	Ph	Ph	78
8m	4-CH₃	4-CH₃C₆H₄	4-ClC₆H₄	77
8n	4-CH₃	4-BrC₆H₄	4-CH₃C₆H₄	73
8o	4-CH₃	2-ClC₆H₄	Ph	61
8p	4-CH₃	4-BrC₆H₄	4-NCC₆H₄	71
8q	4-CH₃	4-BrC₆H₄	i-Pr	55
8r	5-Cl	4-BrC₆H₄	4-CH₃C₆H₄	77
8s	H	4-CH₃OC₆H₄	Ph	50
8t	H	4-NO₂C₆H₄	Ph	0

Product	R¹	Ar	R²	Yield^a/%
8a	H	Ph	Ph	75
8b	H	Ph	4-CH₃C₆H₄	73
8c	H	Ph	4-ClC₆H₄	72
8d	H	4-BrC₆H₄	2-BrC₆H₄	63
8e	H	4-BrC₆H₄	4-CH₃OC₆H₄	64
8f	H	4-BrC₆H₄	CH₃	80
8g	H	4-BrC₆H₄	Bu	69
8h	H	4-BrC₆H₄	i-Pr	49
8i	H	4-CH₃C₆H₄	Thiophen-2-yl	80
8j	H	4-CH₃C₆H₄	Cyclohexyl	56
8k	4-CH₃	Ph	Ph	74
8l	5-Cl	Ph	Ph	78
8m	4-CH₃	4-CH₃C₆H₄	4-ClC₆H₄	77
8n	4-CH₃	4-BrC₆H₄	4-CH₃C₆H₄	73
8o	4-CH₃	2-ClC₆H₄	Ph	61
8p	4-CH₃	4-BrC₆H₄	4-NCC₆H₄	71
8q	4-CH₃	4-BrC₆H₄	i-Pr	55
8r	5-Cl	4-BrC₆H₄	4-CH₃C₆H₄	77
8s	H	4-CH₃OC₆H₄	Ph	50
8t	H	4-NO₂C₆H₄	Ph	0

三组分一锅法合成3,4-二氢喹唑啉衍生物

One-Pot Three-Component Synthesis of 3,4-Dihydroquinazoline Derivatives

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Entry^a	Solvent	Temp./℃	Yield^b/%
1	CH₂Cl₂	25	75
2	CH₃CN	25	68
3	1,4-Dioxane	25	67
4	Toluene	25	60
5	THF	25	55
6	DMF	25	35
7	CH₂Cl₂	0	70
8	CH₂Cl₂	40	74

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