Scientific Reports

Table 4 Synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-triones.

From: A straightforward, environmentally beneficial synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]-2′,10,12-triones mediated by a nano-ordered reusable catalyst


Entry	R¹	R²	R³	R⁴	Product	Time, min	Yield, %	Melting point, °C
1	H	H	H	H	4a	20	95	> 300
2	OMe	H	H	H	4b	15	97	> 300
3	NO₂	H	H	H	4c	25	90	> 300
4	Cl	H	H	H	4d	20	92	> 300
5	Me	H	H	H	4e	18	95	> 300
6	Br	H	H	H	4f	20	92	> 300
7	H	H	Cl	H	4g	20	92	> 300
8	OMe	H	Cl	H	4h	15	94	> 300
9	Me	H	Cl	H	4i	18	93	> 300
10	Cl	H	Cl	H	4j	20	91	> 300
11	H	H	Br	H	4k	25	90	> 300
12	OMe	H	Br	H	4l	18	94	> 300
13	Me	H	Br	H	4m	20	93	> 300
14	Cl	H	Br	H	4n	22	92	> 300
15	H	H	NO₂	H	4o	30	89	> 300
16	OMe	H	NO₂	H	4p	20	90	> 300
17	Me	H	NO₂	H	4q	20	90	> 300
18	Cl	H	NO₂	H	4r	25	88	> 300
19	H	H	H	Me	4s	22	89	> 300
20	OMe	H	H	Me	4t	20	92	> 300
21	Me	H	H	Me	4u	20	90	> 300
22	Cl	H	H	4-Tol	4v	25	89	> 300
23	OMe	H	H	Bn	4w	30	85	> 300
24	OMe	H	H	4-BrC₆H₄CH₂	4x	35	80	> 300
25	H	OMe	H	H	4y	15	94	> 300

Reaction conditions: isatin (1, 1 mmol), 1,3-indanedione (2, 2 mmol) and aniline (3, 1 mmol), MCM-41-SO₃H (20 mg), DMF (1 mL), 100 °C.

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