Double aza-Morita-Baylis-Hillman Domino Reaction to Access Amino Derived 1,6-Dienes

doi:10.6023/cjoc202010036

Abstract

Aza-Morita-Baylis-Hillman reaction plays specific roles in the construction of C—C bond, and their applications in synthetic chemistry and pharmaceutical chemistry have also been well-documented. Herein, a novel 1,4-diazabicyclo- [2.2.2]octane (DABCO) mediated doubleaza-Morita-Baylis-Hillman cascade strategy toward synthetically important aza-MBH adducts is reported. Complementary to classical aza-MBH reaction, this protocol employs a wide variety of primary amines including benzyl, alkyl and aryl moieties as the reaction partners, giving an efficient alternative to produce amino derived 1,6-dienes in moderate to high yields in the presence of formaldehyde and α,β-unsaturated carbonyl compounds. Rather surprisingly, using an aqueous medium has proven to be successful in promoting the reaction efficiency and achieving a higher yield of target products. One-pot operation, high chemoselectivity, short reaction time, and broad substrate scope of primary amines exemplified the significant advances and practicability of this protocol.

Key words: aza-Morita-Baylis-Hillman reaction, domino reaction, primary amine, 1,6-diene

Cite this article

Futao Peng, Liliang Huang, Junhai Huang, Huangdi Feng. Double aza-Morita-Baylis-Hillman Domino Reaction to Access Amino Derived 1,6-Dienes[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2001-2007.

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Entry	Ratio of 1a/2a/3a	Additive	Solvent (V:V)	Yield^b/%
1	0.5:2.0:3.0	DABCO	Toluene	45
2	0.5:2.0:3.0	DBU	Toluene	18
3	0.5:2.0:3.0	DIEPA	Toluene	12
4	0.5:2.0:3.0	DMEDA	Toluene	11
5	0.5:2.0:3.0	DMAP	Toluene	15
6	0.5:2.0:3.0	PPh₃	Toluene	20
7	0.5:2.0:3.0	P(C₅H₁₁)₃	Toluene	5
8	0.5:2.0:3.0	DABCO	DMSO	19
9	0.5:2.0:3.0	DABCO	Dioxane	9
10	0.5:2.0:3.0	DABCO	THF	40
11	0.5:2.0:3.0	DABCO	EtOH	30
12	0.5:2.0:3.0	DABCO	CH₃CN	18
13	0.5:1.0:3.0	DABCO	Toluene	6
14	0.5:1.5:3.0	DABCO	Toluene	31
15	0.5:2.5:3.0	DABCO	Toluene	67
16	0.5:2.5:2.5	DABCO	Toluene	52
17	0.5:2.5:3.5	DABCO	Toluene	40
18^c	0.5:2.5:3.0	DABCO	Toluene	81
19	0.5:2.5:3.0	DABCO	Toluene/H₂O (24:1)	80
20	0.5:2.5:3.0	DABCO	Toluene/H₂O (16:1)	85
21	0.5:2.5:3.0	DABCO	Toluene/H₂O (8:1)	65
22^d	0.5:2.5:3.0	DABCO	Toluene	0

Entry	Ratio of 1a/2a/3a	Additive	Solvent (V:V)	Yield^b/%
1	0.5:2.0:3.0	DABCO	Toluene	45
2	0.5:2.0:3.0	DBU	Toluene	18
3	0.5:2.0:3.0	DIEPA	Toluene	12
4	0.5:2.0:3.0	DMEDA	Toluene	11
5	0.5:2.0:3.0	DMAP	Toluene	15
6	0.5:2.0:3.0	PPh₃	Toluene	20
7	0.5:2.0:3.0	P(C₅H₁₁)₃	Toluene	5
8	0.5:2.0:3.0	DABCO	DMSO	19
9	0.5:2.0:3.0	DABCO	Dioxane	9
10	0.5:2.0:3.0	DABCO	THF	40
11	0.5:2.0:3.0	DABCO	EtOH	30
12	0.5:2.0:3.0	DABCO	CH₃CN	18
13	0.5:1.0:3.0	DABCO	Toluene	6
14	0.5:1.5:3.0	DABCO	Toluene	31
15	0.5:2.5:3.0	DABCO	Toluene	67
16	0.5:2.5:2.5	DABCO	Toluene	52
17	0.5:2.5:3.5	DABCO	Toluene	40
18^c	0.5:2.5:3.0	DABCO	Toluene	81
19	0.5:2.5:3.0	DABCO	Toluene/H₂O (24:1)	80
20	0.5:2.5:3.0	DABCO	Toluene/H₂O (16:1)	85
21	0.5:2.5:3.0	DABCO	Toluene/H₂O (8:1)	65
22^d	0.5:2.5:3.0	DABCO	Toluene	0

aza-Morita-Baylis-Hillman反应二次串联构建氨基衍生的1,6-二烯化合物