Three-Component Reaction for Efficient Synthesis of Functionalized Spiro[cyclopentane-1,3'-indolines]

doi:10.6023/cjoc202103034

Abstract

The three-component reaction of alkylisocyanide, dialkyl acetylenedicarboxylate (alkyl propiolate) and 3-phenacylideneoxindole in refluxing toluene afforded the functionalized spiro[cyclopentane-1,3'-indolines] in satisfactory yields. However, the similar reaction of 3-phenacylideneoxindoles with unsubstituted NH group resulted in spiro[cyclopentane-1,3'-indolines] with additional aza-buta-1,3-diene scaffold. On the other hand, the three-component reactions with 3-arylideneoxindolin- 2-ones only gave 2-(2-oxoindolin-1-yl)-3-((alkylimino)methylene)succinates. It was also interesting to find that the reaction of free amino group in two kinds of functionalized 3-methyleneoxindoles with alkylisocyanide and dialkyl acetylenedicarboxylate selectively gave C2-substituted 1-aza-buta-1,3-diene (C=C—C=NR) or C4-substituted 1-aza-buta-1,2-diene (C—C=C=NR) scaffold in the molecules.

Key words: isocyanide, dialkyl acetylenedicarboxylate, 3-phenacylideneoxindole, spiro[cyclopentane-1,3'-indoline], multicomponent reaction

Cite this article

Weiqing Ma, Ying Han, Jin Sun, Chaoguo Yan. Three-Component Reaction for Efficient Synthesis of Functionalized Spiro[cyclopentane-1,3'-indolines][J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3180-3191.

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Entry	Solvent	Temp./	Time/h	Yield^b/%
1	CH₂Cl₂	r.t.	12	34
2	MeCN	r.t.	12	36
3	PhMe	r.t.	12	42
4	THF	r.t.	12	—
5	EtOH	r.t.	12	—
6	MeOH	r.t.	12	—
7	THF	60	12	—
8	MeCN	60	6	45
9	PhMe	60	2	70
10	PhMe	110	0.5	86
11	PhMe	110	2	83

Entry	Solvent	Temp./	Time/h	Yield^b/%
1	CH₂Cl₂	r.t.	12	34
2	MeCN	r.t.	12	36
3	PhMe	r.t.	12	42
4	THF	r.t.	12	—
5	EtOH	r.t.	12	—
6	MeOH	r.t.	12	—
7	THF	60	12	—
8	MeCN	60	6	45
9	PhMe	60	2	70
10	PhMe	110	0.5	86
11	PhMe	110	2	83

Compd.	R¹	R²	R³	E	Yield^b/%
1a	Cyclohexyl	H	Bn	p-CH₃C₆H₅	82
1b	Cyclohexyl	Cl	Bn	p-CH₃OC₆H₅	86
1c	Cyclohexyl	Cl	Bn	p-CH₃C₆H₅	82
1d	Cyclohexyl	F	Bn	p-CH₃OC₆H₅	78
1e	Cyclohexyl	F	Bn	p-CH₃C₆H₅	75
1f	Cyclohexyl	F	n-Bu	C₆H₅	62
1g	t-Bu	Cl	Bn	p-CH₃OC₆H₅	85
1h	t-Bu	Cl	Bn	p-CH₃C₆H₅	80
1i	t-Bu	F	Bn	p-CH₃C₆H₅	72
1j	t-Bu	Cl	Bn	OCH₂CH₃	75
1k	t-Bu	CH₃	Bn	OCH₂CH₃	71
1l	t-Bu	H	Bn	OCH₃	69
1m	t-Bu	Cl	Bn	OCH₃	78

Compd.	R¹	R²	R³	E	Yield^b/%
1a	Cyclohexyl	H	Bn	p-CH₃C₆H₅	82
1b	Cyclohexyl	Cl	Bn	p-CH₃OC₆H₅	86
1c	Cyclohexyl	Cl	Bn	p-CH₃C₆H₅	82
1d	Cyclohexyl	F	Bn	p-CH₃OC₆H₅	78
1e	Cyclohexyl	F	Bn	p-CH₃C₆H₅	75
1f	Cyclohexyl	F	n-Bu	C₆H₅	62
1g	t-Bu	Cl	Bn	p-CH₃OC₆H₅	85
1h	t-Bu	Cl	Bn	p-CH₃C₆H₅	80
1i	t-Bu	F	Bn	p-CH₃C₆H₅	72
1j	t-Bu	Cl	Bn	OCH₂CH₃	75
1k	t-Bu	CH₃	Bn	OCH₂CH₃	71
1l	t-Bu	H	Bn	OCH₃	69
1m	t-Bu	Cl	Bn	OCH₃	78

Compd.	R¹	R²	Ar	Yield^b/% (Z∶E)
2a	Cyclohexyl	CH₃	p-CH₃OC₆H₅	63 (1∶9)
2b	Cyclohexyl	H	p-CH₃C₆H₄	59 (1∶9)
2c	t-Bu	Cl	p-CH₃C₆H₄	70 (1∶9)
2d	t-Bu	CH₃	p-ClC₆H₄	64 (1∶9)
2e	t-Bu	F	p-CH₃OC₆H₅	67 (1∶9)

三组分反应高效合成螺[环戊烷-1,3'-吲哚啉]衍生物