Optimization the reaction condition of annulation of 1a with 2^a.

Entry	Base catalyst	Solvent	Conv. heating		Sonication		MW irradiation
			Yielde %	Time (h)	Yielde %	Time (min)	Yielde %	Time (min)
1	Et3Nb	EtOH	66	4	70	70	75	7
2	Et3Nc	EtOH	74f	2	79g	50	87h	5
3	Et3Nd	EtOH	70	3	73	60	80	6
4	Et3Nc	MeOH	55	6	60	80	70	10
5	Et3Nc	i-PrOH	68	7	72	80	80	10
6	Et3Nc	n-Hexane	28	9	30	100	40	15
7	Et3Nc	1,4-Dioxane	38	8	40	100	45	15
8	Et3Nc	DMF	42	9	45	110	55	20
9	Et3Nc	Toluene	34	8	37	100	42	15
10	Pyridinec	EtOH	55i	6	60j	80	75k	15
11	DABCOc	EtOH	30	11	35	110	41	20
12	DBUc	EtOH	30	11	36	110	46	20
13	NaHCO3c	EtOH	34	9	36	90	42	12
14	K2CO3c	EtOH	38	7	40	90	45	15
15	NaOHc	EtOH	30	7	30	100	40	15

^aReaction conditions: phenylhydrazonopropanal 1a (2 mmol), acetoacetanilide 2 (4 mmol), solvent (15 mL) and base (10–30 mol%), conventional heating at reflux for 2–11 h, ultrasound at 80 °C for 50–110 min, microwave irradiation at 80 °C (200 W) for 5–20 min.

^bBase 10 mol%.

^cBase 20 mol%.

^dBase 30 mol%.

^eIsolated yields.

^fYield was 12% after 20 min and 50% after 80 min.

^gYield was 30% after 20 min and 62% after 40 min.

^hYield was 53% after 3 min.

ⁱYield was 17% after 2 h.

^jYield was 38% after 50 min.

^kYield was 25% after 5 min.